Derivatives of phenylacetic acid, their preparation and their use as pesticides

ABSTRACT

Compounds of the formula I ##STR1## where n, W, X, Y, Z, R 1 , R 2 , and R 3  are as defined herein exhibit fungicidal, insecticidal, and acaracidal activity.

The present invention relates to novel phenylacetic acetic acidderivatives having fungicidal, insecticidal and acaricidal activity,fungicides containing these compounds and methods for controlling thefungi.

It is known (for example from European Patents 178,826, 253,213 and280,185) that esters of acrylic acid, crotonic acid ormethoxyiminoacetic acid can be used as fungicides. However, the actionof these compounds is unsatisfactory in many cases.

We have found that novel phenylacetic acid derivatives of the generalformula I have excellent fungicidal activity and in additioninsecticidal and acaricidal activity. ##STR2##

In formula I,

n is 0 or 1,

W may occupy any free position on the benzene ring and is hydrogen,halogen, such as fluorine, chlorine, bromine or iodine, unsubstituted orsubstituted C₁ -C₄ -alkyl, such as methyl, ethyl, n-propyl, isopropyl,n-butyl, isobutyl, sec-butyl or tert-butyl, unsubstituted or substitutedC₁ -C₄ -alkoxy, such as methoxy, ethoxy, n-propoxy, isopropoxy,n-butoxy, isobutoxy, sec-butoxy or tert-butoxy, preferably hydrogen,chlorine, methyl or methoxy, particularly preferably hydrogen,

X is CHOCH₃, NOCH₃, CHCH₃ or CHC₂ H₅,

Y is oxygen, sulfur or NR⁴, --O--NR⁴, --NR⁴ --O-- or NR⁴ --NR⁵,preferably oxygen, sulfur or NR⁴, particularly preferably oxygen or NR⁴,

Z is oxygen, NR⁶, NOR⁷ or N--NR⁸ R⁹ or, if n is 1, furthermore sulfur,preferably oxygen or NOR⁷ or N--NR⁸ R⁹, particularly preferably oxygenor NOR⁷,

R¹ is hydrogen or unsubstituted or substituted C₁ -C₄ -alkyl as statedabove, preferably hydrogen or methyl, particularly preferably hydrogen,

R² is independent of R¹ and is hydrogen, unsubstituted or substituted C₁-C₄ -alkyl as stated above, unsubstituted or substituted C₃ -C₆-cycloalkyl, such as cyclopropyl, cyclobutyl, cyclopentyl andcyclohexyl, unsubstituted or substituted and/or fused aryl, such asphenyl, naphthyl, anthryl or phenanthryl, unsubstituted or substitutedand/or fused hetaryl, such as 2-pyridyl, 3-pyridyl, 4-pyridyl,2-quinolyl, 1-isoquinolyl, pyrazinyl, 2-pyrimidinyl, 4-pyrimidinyl,2-quinoxalinyl, 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 2-furyl, 3-thienyl,3-pyrazolyl, 5-pyrazolyl, 1-imidazolyl, 4-imidazolyl,1,2,4-triazol-3-yl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 3-isoxazolyl,2-thiazolyl, 4-isothiazolyl, 1,3,4-oxadiazolyl, 1,3,4-thiadiazolyl,2-indolyl, 3-indolyl, 2-benzothiazolyl, 9-carbazolyl or 2-pteridinyl, C₁-C₄ -perfluoroalkyl, such as trifluoromethyl, pentafluoroethyl,heptafluoroisopropyl or nonafluoro-n-butyl, or CO--V .

R² is preferably hydrogen, C₁ -C₄ -alkyl or CO--V, particularlypreferably hydrogen.

R³ is

hydrogen,

unsubstituted or substituted C₁ -C₄ -alkyl as stated above,unsubstituted or substituted C₂ -C₄ -alkenyl, such as ethenyl,propen-1-yl, propen-2-yl, propen-3-yl, 2-buten-1-yl or2-methylpropen-1-yl,

unsubstituted or substituted C₃ -C₆ -cycloalkyl as stated above,

unsubstituted or substituted 3-membered to 6-membered heterocyclyl, suchas oxiranyl, azetidinyl, tetrahydrofuran-2-yl, pyrrolidin-1-yl orthiopyran-4-yl,

unsubstituted or substituted and/or fused aryl as stated above,

unsubstituted or substituted and/or fused hetaryl as stated above,

unsubstituted or substituted aryl-C₁ -C₄ -alkyl, such as benzyl,1-phenylethyl, 2-phenylethyl, 4-phenyl-n-butyl,2-phenyl-2-methylprop-1-yl or naphthylmethyl,

unsubstituted or substituted hetaryl-C₁ -C₄ -alkyl, such aspyrid-2-ylmethyl, 2-fur-3-ylethyl, 3-isoxazol-5-ylpropyl or1-indolylmethyl,

unsubstituted or substituted aryl-C₂ -C₄ -alkenyl, such as1-phenylethenyl or 1-naphth-3-ylprop-1-en-3-yl, or

unsubstituted or substituted hetaryl-C₂ -C₄ -alkenyl, such as2-pyrid-4-ylethenyl or 1-thien-3-ylethenyl, or, if n is 0, furthermorecyano, C₁ -C₄ -perfluoroalkyl or unsubstituted or substituted C₂ -C₄-alkynyl, such as ethynyl, propyn-1-yl, propyn-3-yl, 1-butyn-4-yl or2-butyn-1-yl or, if n is 1 and Y is oxygen, furthermore unsubstituted orsubstituted trialkylsilyl, such as trimethylsilyl, triethylsilyl,tert-butyldimethylsilyl or di-tert-butylmethylsilyl.

R³ is preferably hydrogen, unsubstituted or substituted C₁ -C₄ -alkyl,unsubstituted or substituted and/or fused aryl, unsubstituted orsubstituted and/or fused hetaryl or unsubstituted or substituted aryl-C₁-C₄ -alkyl,

particularly preferably hydrogen, C₁ -C₄ -alkyl, unsubstituted orsubstituted phenyl or unsubstituted or substituted benzyl,

R⁴ and R⁵ are independent of one another and are each hydrogen,

unsubstituted or substituted C₁ -C₄ -alkyl as stated above or

unsubstituted or substituted C₃ -C₆ -cycloalkyl as stated above,

preferably hydrogen, methyl or ethyl,

R⁶ is unsubstituted or substituted C₁ -C₄ -alkyl as stated above or

unsubstituted or substituted and/or fused aryl or hetaryl as statedabove,

preferably substituted phenyl,

R⁷ and R⁸ are each

hydrogen,

unsubstituted or substituted C₁ -C₄ -alkyl as stated above,

unsubstituted or substituted C₂ -C₄ -alkenyl as stated above,

unsubstituted or substituted C₂ -C₄ -alkynyl as stated above,

unsubstituted or substituted C₃ -C₆ -cycloalkyl as stated above,

unsubstituted or substituted and/or fused aryl as stated above,

unsubstituted or substituted and/or fused hetaryl as stated above,

unsubstituted or substituted aryl-C₁ -C₄ -alkyl as stated above,

unsubstituted or substituted hetaryl-C₁ -C₄ -alkyl as stated above,

or COR¹⁰.

R⁷ is preferably hydrogen, unsubstituted or substituted C₁ -C₄ -alkyl,unsubstituted or substituted C₂ -C₄ -alkenyl, unsubstituted orsubstituted aryl-C₁ -C₄ -alkyl or unsubstituted or substitutedhetaryl-C₁ -C₄ -alkyl, particularly preferably C₁ -C₄ -alkyl orunsubstituted or substituted benzyl, and

R⁸ is preferably hydrogen, unsubstituted or substituted C₁ -C₄ -alkyl orunsubstituted or substituted aryl, particularly preferably unsubstitutedor substituted phenyl, R⁹ has the same general and preferred meanings asR⁴ and is independent of R⁸,

R¹⁰ is

unsubstituted or substituted C₁ -C₄ -alkyl as stated above,

unsubstituted or substituted C₃ -C₆ -cycloalkyl as stated above,

unsubstituted or substituted aryl as stated above or

unsubstituted or substituted hetaryl as stated above,

preferably unsubstituted or substituted C₁ -C₄ -alkyl or unsubstitutedor substituted aryl, particularly preferably methyl or unsubstituted orsubstituted phenyl,

V is

unsubstituted or substituted C₁ -C₄ -alkyl as stated above,

unsubstituted or substituted aryl as stated above,

unsubstituted or substituted hetaryl as stated above, hydroxyl,

unsubstituted or substituted C₁ -C₄ -alkoxy as stated above,

unsubstituted or substituted allyloxy,

unsubstituted or substituted benzyloxy or

unsubstituted or substituted trimethylsilyloxy.

The bond between the two carbon atoms carrying R¹ and R² may be a singleor a double bond. The double bond is preferred.

The radicals indicated as being unsubstituted or substituted can carry,in any position, one or more, preferably one to three, substituents,which are identical or different. These substituents are

hydrogen, halogen, cyano, nitro,

alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heteroaryl, heterocyclyl,haloalkyl,

hydroxyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyloxy, aryloxy,heteroaryloxy, heterocyclyloxy, haloalkoxy,

mercapto, alkylthio, alkenylthio, alkynylthio, cycloalkylthio, arylthio,heteroarylthio, heterocyclylthio,

haloalkylthio,

amino, alkylamino, alkenylamino, alkynylamino, cycloalkylamino,arylamino, heteroarylamino, heterocyclylamino, dialkylamino,N-alkyl-arylamino, N-alkyl-heteroarylamino,

formyl, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl,cycloalkylcarbonyl, arylcarbonyl, heteroarylcarbonyl,heterocyclylcarbonyl,

carboxyl, alkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl,cycloalkyloxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl,heterocyclyloxy-carbonyl,

formyloxy, alkylcarbonyloxy, alkenylcarbonyloxy, alkynylcarbonyloxy,cycloalkylcarbonyloxy, arylcarbonyloxy, heteroarylcarbonyloxy,heterocyclylcarbonyloxy,

aminocarbonyl, alkylaminocarbonyl, alkenyl-aminocarbonyl,alkynylaminocarbonyl, cycloalkylamino-carbonyl, arylaminocarbonyl,heteroarylaminocarbonyl, heterocyclylaminocarbonyl,dialkylaminocarbonyl, N-alkyl-arylaminocarbonyl,N-alkyl-heteroarylaminocarbonyl,

hydroxylaminocarbonyl, alkoxyaminocarbonyl, alkenyloxyaminocarbonyl,alkynyloxyaminocarbonyl,

formamido, alkyl-carbonylamino, alkenylcarbonylamino,alkynylcarbonyl-amino, cycloalkylcarbonylamino, arylcarbonylamino,heteroarylcarbonylamino, heterocyclylcarbonylamino,alkylcarbonyl-N-alkylamino, arylcarbonyl-N-alkylamino,heteroarylcarbonyl-N-alkylamino,

aminothiocarbonyl, alkylamino-thiocarbonyl, dialkylaminothiocarbonyl,

alkylsulfoxyl, arylsulfoxyl, heteroarylsulfoxyl,

alkylsulfonyl, aryl-sulfonyl, heteroarylsulfonyl, hydroxysulfinyl,alkoxysulfinyl,

hydroxysulfonyl, alkoxysulfonyl,

alkylsulfinyloxy, arylsulfinyloxy, heteroarylsulfinyloxy,

alkyl-sulfonyloxy, arylsulfonyloxy, heteroaryl sulfonyloxy,

dialkoxyphosphinyl, bis(aryloxy)phosphinyl,

trialkylsilyl, trialkylsilyloxy,

or a fragment of the formula R'--O--N═CR", in which R' and R"independently of one another are hydrogen, alkyl, alkenyl or alkynyland, is R' is not hydrogen, R" can also be alkoxy.

In the abovementioned substituents, halogen and the organicsubstructures, for example ethyl, each have the abovementioned meanings.The substituents can in turn be substituted by one or more of theabovementioned radicals.

The novel compounds of the formula I may be obtained in the preparationas mixtures of stereoisomers (E/Z isomers at C═C or C═N double bonds,diastereomers, enantiomers), which can be separated into theirindividual components in a conventional manner, for example bycrystallization or chromatography. Both the individual isomers and themixtures thereof can be used as fungicides, insecticides or acaricides,and the present invention relates to all of them. The fungicidalactivity is preferred.

The present invention preferably relates to novel compounds of thegeneral formula II ##STR3## where W may occupy any free position on thebenzene ring and is hydrogen, chlorine, methyl or methoxy, preferablyhydrogen,

X is CHOCH₃, NOCH₃, CHCH₃ or CHC₂ H₅,

Z is oxygen, NR⁶, NOR⁷ or N--NR⁸ R⁹, preferably oxygen or NOR⁷,

R¹ and R² are independent of one another and are each hydrogen or C₁ -C₄-alkyl as stated above, preferably hydrogen,

R³ is hydrogen, unsubstituted or substituted C₁ -C₄ -alkyl,unsubstituted or substituted C₂ -C₄ -alkenyl, unsubstituted orsubstituted C₂ -C₄ -alkynyl, unsubstituted or substituted C₃ -C₆-cycloalkyl, unsubstituted or substituted 3-membered to 6-memberedheterocyclyl, unsubstituted or substituted and/or fused aryl,unsubstituted or substituted and/or fused hetaryl, unsubstituted orsubstituted aryl-C₁ -C₄ -alkyl, unsubstituted or substituted hetaryl-C₁-C₄ -alkyl, unsubstituted or substituted aryl-C₂ -C₄ -alkenyl orunsubstituted or substituted hetaryl-C₂ -C₄ -alkenyl, in each case asstated above, preferably hydrogen, unsubstituted or substituted C₁ -C₄-alkyl, unsubstituted or substituted aryl, unsubstituted or substitutedhetaryl, particularly preferably C₁ -C₄ -alkyl or unsubstituted orsubstituted phenyl,

R⁴ is hydrogen unsubstituted or substituted C₁ -C₄ -alkyl orunsubstituted or substituted C₃ -C₆ -cycloalkyl, in each case as statedabove, preferably hydrogen, methyl or ethyl,

R⁶ is unsubstituted or substituted C₁ -C₄ -alkyl or unsubstituted orsubstituted and/or fused aryl or hetaryl, in each case as stated above,preferably unsubstituted or substituted phenyl,

R⁷ and R⁸ are each hydrogen, unsubstituted or substituted C₁ -C₄ -alkyl,unsubstituted or substituted C₂ -C₄ -alkenyl, unsubstituted orsubstituted C₂ -C₄ -alkynyl, unsubstituted or substituted C₃ -C₆-cycloalkyl, unsubstituted or substituted and/or fused aryl,unsubstituted or substituted and/or fused hetaryl, unsubstituted orsubstituted aryl-C₁ -C₄ -alkyl, unsubstituted or substituted hetaryl-C₁-C₄ -alkyl, in each case as stated above, or COR¹⁰,

R⁷ preferably being hydrogen, unsubstituted or substituted C₁ -C₄-alkyl, unsubstituted or substituted C₂ -C₄ -alkenyl, or unsubstitutedor substituted aryl-C₁ -C₄ -alkyl, particularly preferably C₁ -C₄ -alkylor unsubstituted or substituted benzyl, and

R⁸ preferably being unsubstituted or substituted C₁ -C₄ -alkyl orunsubstituted or substituted aryl-C₁ -C₄ -alkyl, particularly preferablyC₁ -C₄ -alkyl or unsubstituted or substituted benzyl,

R⁹ has the same general and preferred meanings as R⁴ and is independentof R⁸ and

R¹⁰ is unsubstituted or substituted C₁ -C₄ -alkyl, unsubstituted orsubstituted C₃ -C₆ -cycloalkyl, unsubstituted or substituted aryl orunsubstituted or substituted hetaryl, in each case as stated above,preferably C₁ -C₄ -alkyl or unsubstituted or substituted phenyl.

The present invention furthermore preferably relates to novel compoundsof the general formula III ##STR4## where W may occupy any free positionon the benzene ring and is hydrogen, chlorine, methyl or methoxy,preferably hydrogen,

X is CHOCH₃, NOCH₃, CHCH₃ or CHC₂ H₅,

Y is oxygen, sulfur or NR⁴, preferably oxygen or NR⁴,

R¹ is hydrogen or C₁ -C₄ -alkyl, preferably hydrogen,

R² is hydrogen, C₁ -C₄ -alkyl or CO--V, preferably hydrogen,

R³ is hydrogen, unsubstituted or substituted C₁ -C₄ -alkyl,unsubstituted or substituted C₁ -C₄ -alkenyl, unsubstituted orsubstituted and/or fused aryl, unsubstituted or substituted and/or fusedhetaryl, unsubstituted or substituted aryl-C₁ -C₄ -alkyl orunsubstituted or substituted hetaryl-C₁ -C₄ -alkyl or,

if Y is oxygen, furthermore trialkylsilyl, in each case as stated above,preferably C₁ -C₄ -alkyl, unsubstituted or substituted phenyl orunsubstituted or substituted benzyl,

R⁴ is hydrogen, unsubstituted or substituted C₁ -C₄ -alkyl orunsubstituted or substituted C₃ -C₆ -cycloalkyl, in each case as statedabove, preferably hydrogen, methyl or ethyl, and

V is hydroxyl, C₁ -C₄ -alkoxy, allyloxy, trialkylsilyloxy orunsubstituted or substituted benzyloxy, in each case as stated above.

In one aspect, the present invention particularly preferably relates tonovel compounds of the general formula IV ##STR5## where X is CHOCH₃,NOCH₃, CHCH₃ or CHC₂ H₅,

Z is oxygen or NOR⁷,

R³ is hydrogen, unsubstituted or substituted C₁ -C₄ -alkyl,unsubstituted or substituted C₂ -C₄ -alkenyl, unsubstituted orsubstituted and/or fused aryl or unsubstituted or substituted and/orfused hetaryl, in each case as stated above, preferably hydrogen, C₁ -C₄-alkyl or unsubstituted or substituted aryl, particularly preferablyhydrogen, methyl or unsubstituted or substituted phenyl,

R⁷ is hydrogen, unsubstituted or substituted C₁ -C₄ -alkyl,unsubstituted or substituted C₂ -C₄ -alkenyl, unsubstituted orsubstituted aryl-C₁ -C₄ -alkyl, preferably unsubstitued or substitutedbenzyl, unsubstituted or substituted hetaryl-C₁ -C₄ -alkyl, preferablymethyl substituted by five-membered hetaryl, in each case as statedabove, or COR¹⁰,

R¹⁰ is unsubstituted or substituted C₁ -C₄ -alkyl, unsubstituted orsubstituted aryl or unsubstituted or substituted hetaryl, in each caseas stated above, preferably C₁ -C₄ -alkyl or unsubstituted orsubstituted phenyl.

The present invention furthermore particularly preferably relates tonovel compounds of the general formula V ##STR6## where X is CHOCH₃,NOCH₃, CHCH₃ or CHC₂ H₅,

Y is oxygen or NR⁴,

R³ is unsubstituted or substituted C₁ -C₄ -alkyl, unsubstituted orsubstituted and/or fused aryl, unsubstituted or substituted and/or fusedhetaryl, unsubstituted or substituted aryl-C₁ -C₄ -alkyl orunsubstituted or substituted hetaryl-C₁ -C₄ -alkyl, in each case asstated above, and

R⁴ is hydrogen or C₁ -C₄ -alkyl, preferably hydrogen, methyl or ethyl.

The novel compounds can be prepared, for example, by the methods shownin the synthesis schemes below. In all schemes, unless restrictions arespecifically mentioned, A is an abbreviation for the group R³ --(Y)_(n)-- defined in claim 1, R is an aliphatic, aromatic or heterocyclicradical and R' may furthermore be hydrogen. B is one of the groups##STR7## or a fragment from which one of these groups can besynthesized. ##STR8## a N-methylmorpholine N-oxide, ΔT b A--COCH₃, baseor acid, if necessary a dehydrating agent

e.g. A--CO--CH₂ --COOtBu, piperidine/p-TsOH, then CF₃ COOH, then ΔT

d A--CO--CH═PR₃ or A--CO--CH₂ P(═O)Z₂ (Z═Ar, O-Alkyl)/base

e LiCH₂ PO(OR)₂, A--CN

f A--CO--CH₂ --CO--A, NaOMe

g H₂, Pd/C

h PdCl₂ (PhCN)₂, AgOSO₂ CF₃ or Sn(OSO₂ CF₃)₂, N-methylmorpholine

ΔT=elevated temperatures, p-TsOH=p-toluenesulfonic acid.

Scheme I shows methods for synthesizing the carbonyl compounds of type 3or 4 (A═H, alkyl, aryl, hetaryl, organyloxy, organylthio or mono- ordiorganylamino). The α,β-unsaturated compounds 3 can advantageously besynthesized from aldehydes 2, which can be achieved by aldol [Org.Synth. Coll. I (1941), 77] or Knoevenagel condensation with subsequentelimination of a carbonyl or carboxyl function [Acta Chem. Scand. 17(1963), 2316], as well as by Wittig [J. Chem. Soc. (1961), 1266] orHorner-Wadsworth-Emmons olefination [Review Org. React. 25 (1977), 73].Chalcones (i.e. A=aryl) can also be synthesized in a one-vessel reactionby reacting lithiomethanephosphonic esters with aromatic nitriles andthe aldehydes 2 [Synthesis (1991), 213].

The aldehydes of type 2 can be prepared by the method described inEuropean Patent 393,428 from the benzyl bromides 1 [for preparation, seeEuropean Patents 226,917, 337,211 and 363,818]. The ketones, esters and1,3-dicarbonyl compounds required for the condensation reactions aregenerally known building blocks of organic synthesis; thecarbonyl-substituted Wittig and Horner reagents are either known or canbe synthesized by methods known from the literature [Ang. Chem. 72(1960), 572 and 73 (1961), 27; Chem. Ber. 95 (1962), 1513; Org. Synth.Coll. VI (1988), 448].

The saturated carbonyl compounds 4 can be prepared from the benzylbromides 1 by reaction with β-dicarbonyl compounds with elimination ofone of the two carbonyl groups (J. Org. Chem. 30 (1965), 3321]; on theother hand, they can be synthesized from the unsaturated analogs 3, forexample by hydrogenation [Org. Synth. Coll. I (1941), 101; J. Am. Chem.Soc.111 (1989), 1063]. Conversely, the preparation ofcarbonyl-substituted alkenes 3 from the analogous alkanes 4 is alsopossible [Chem. Lett. (1983), 1207].

The methods denoted by a, b, d, f and g in Scheme I are also suitablefor the preparation of the substances which are analogous to thecompounds 2, 3 and 4 and in which R¹ and R² (cf. claim 1, 7 or 8) arenot hydrogen. ##STR9## a RNH₂, H⁺, dehydration (azeotropic distillation,molecular sieve)

b RR'N--NH₂.HCl or .H₂ SO₄, ΔT

c H₂ NOH.HCl, ΔT and/or

d H₂ NOR.HCl, ΔT and/or auxiliary base (e.g. pyridine)

e R--Br, base (eg. NaOCH₃, K₂ CO₃)

f R--COCl, pyridine

Scheme II shows possibilities for converting the aldehdyes and ketonesof type 3a (A═H, organyl) into the N-functional derivatives by standardmethods. Thus, imines 5 [Bull. Soc. Chim. Belg. 81 (1972), 643],hydrazones 6 [J. Am. Chem. Soc. 90 (1968), 6821] and oximes [Helv. Chim.Acta 60 (1977), 2294] 7b and oxime ethers 7b [J. Org. Chem. 38 (1973),3749] are obtainable by condensation of the carbonyl compounds 3a withamines, hydrazines and hydroxylamines or alkoxyamines. For thepreparation of the oxime ethers 7b, a two-stage synthesis (conversion of3a to free oxime 7a, followed by O-alkylation [Helv. Chim. Acta 60(1977), 2294]) may be advantageous. Oxime esters 7c can likewise beobtained from the oximes 7a by reaction with an acyl chloride/pyridine[J. Org. Chem. 33 (1968), 150].

The reactions described in Scheme II are also suitable for thepreparation of analogous compounds in which R¹ and/or R² are not H.##STR10## a CF₃ COOH, ΔT b PdCl₂ or Pd(OOCCH₃)₂, PPh₃

c RR'NH, carboxyl-activating agent (eg. di-2-pyridyl disulfide or Ph₂P(═O)Cl)

d R--Br, base (eg. K₂ CO₃)

RSH, carboxyl-activating agent (eg. dicyclohexylcarbodiimide)

f chlorinating agent (eg. SOCl₂), ΔT

g RR'NH; if necessary+pyridine, N(C₂ H₅)₃

h ROH, pyridine N(C₂ H₅)₃

i RSH, pyridine, N(C₂ H₅)₃

The synthesis of cinnamic acid derivatives of type 3 (A═OR, SR, NRR') isillustrated in Scheme III. It is advantageously carried out viacarboxylic esters 9a (corresponding to type 3 with A═OR) which can beprepared according to Scheme I and can be hydrolyzed under nonbasicconditions to give the acid 10, for example tert-butyl esters [in acidicmedium, J. Am. Chem. Soc. 99 (1977), 2353] or allyl esters [withpalladium compounds, Tetrahedron Lett. (1979), 613]. The carboxylicacids 10 can be converted by known methods to, inter alia, mono- ordisubstitutedamides 12 [Tetrahedron Lett. (1970), 1901; Synthesis(1980), 385], other esters 9b [European Patent 310,954 and Synthesis(1975), 805] or thioesters 13 [J. Chem. Soc. (C) (1966), 540]. Thepreparation of such derivatives can also be carried out by the generallyknown method via the acyl chloride 11 (obtainable by reacting thecarboxylic acid 10 with a chlorinating agent, such as thionyl chloride,phosphorus trichloride, phosphoryl chloride or phosgene) by anucleophilic substitution of the chlorine atom in 11.

The reactions described in Scheme III are also suitable for thepreparation of analogous compounds in which R¹ and/or R² are not H.

The reaction routes shown in Schemes II and III are also suitable forconverting the saturated carbonyl compounds 4 into the correspondingderivatives. Conversion of the (α,β-unsaturated) products described inthe two schemes into their saturated analogs is also possible undersuitable hydrogenating or reduction conditions.

Preparation Examples for selected compounds EXAMPLE 1 Methyl2-methoximino-2-{2-[3-oxoprop-(E)1-enyl]-phenyl}-acetate (compound No.77 from Table I)

26.4 g (120 mmol) of methyl 2-methoximino-2-(2-formylphenyl)-acetate(for preparation, see European Patent 393,428, page 3) and 45.6 g oftriphenylphosphoranylideneacetaldehyde in 500 ml of toluene are stirredunder nitrogen for 20 hours at 60° C. The mixture is cooled and thenevaporated down, the residue is taken up in tert-butyl methylether/n-hexane, the insoluble substance (triphenylphosphine oxide) isfiltered off under suction, the filtrate is evaporated down, diethylether is added and the flask is placed in an ice bath. Precipitated Ph₃PO is likewise filtered off under suction, and the filtrate isevaporated down. Column chromatography (from 95:5 to 90:10cyclohexane/ethyl acetate) gives 23.8 g (80%) of the title compound asyellowish crystals of melting point 90°-94° C. The product iscontaminated with about 10% of the vinylog methyl2-methoximino-2-{2-[5-oxopenta-(E)1,(E)3-dienyl]-phenyl}-acetate.

¹ H-NMR (CDCl₃, δ scale): 3.88 and 4.04 (2 s, each 3H, COOCH₃ andNOCH₃); 6.70 (dd, 1H, CH═CH--CHO), 7.1-7.7 (m, together 5H, aromaticprotons and CH═CH--CHO); 9.66 (d, 1H, CHO)

EXAMPLE 2 Methyl2-methoximino-2-{2-[3-(2-chloroprop-2-enyloximino-prop-(E)1-enyl]-phenyl}-acetate(compound No. 57 from Table VI)

3.7 g (15 mmol) of methyl2-methoximino-2-{2-[3-oxoprop-(E)1-enyl]-phenyl}-acetate (Example 1) and2.3 g (15mmol) of 2-chloroprop-2-enyloxyamine hydrochloride in 200 ml oftetrahydrofuran (THF) are refluxed for 1 hour. The mixture is allowed tocool, washed twice with saturated sodium chloride solution, dried overmagnesium sulfate and evaporated down. Purification by columnchromatography (9:1 cyclohexane/ethyl acetate, KG 60) gives the titlecompound (yellow oil, 2.9 g/58%) as a 4:1 mixture of the anti and synisomers of the oxime ether.

¹ H-NMR (CDCl₃, δ scale), anti-isomer: 3.88 and 4.04 (2 s, each 3H,COOCH₃ and NOCH₃); 4.76 (s, 2H, H₂ C═CCl--CH₂ O); 5.42 and 5.48 (2 s,each 1H, H₂ C═CCl); 6.60 and 6.82 (2 d, each 1H, CH═CH--C═N), 7.1-7.8(m, 4H, aromatic protons); 7.92 (d, 1H, CH=N)

EXAMPLE 3 Methyl 2-{2-[3-oxobut-(E)1-enyl]-phenyl}-3-methoxyprop-(E)2-enoate (compound No. 2 from Table I)

29 g (130 mmol) of methyl (2-formylphenyl)-3-methoxyprop-(E)2-enoate(for preparation, see European Patent 393,428, page 3) and 3.9 g (120mmol) of triphenylphosphoranylideneacetone in 500 ml of toluene arestirred under nitrogen for 14 hours at 65° C. The mixture is allowed tocool and is evaporated down, the residue is taken up in diethyl ether,the solid (mainly Ph₃ PO) is filtered off under suction and the solventis stripped off under reduced pressure. Column chromatography gives thetitle compound (21.4 g/69%) as a brownish oil, sufficiently pure forfurther reactions. A crystalline product (mp. 69°-71° C.) is obtained byrecrystallization from ether/pentane.

¹ H-NMR (CDCl₃, d scale): 2.32 (s, 3H, CH₃ --C═O); 3.71 and 3.81 (2 s,each 3H, COOCH₃ and CH--OCH₃); 6.70 (d, 1H, CH═CH--C═O), 7.2-7.5 (m,together 3H) and 7.72 (d, 1H; aromatic protons); 7.53 (d, 1H,CH═CH--C═O); 7.68 (s, 1H, CH--OCH₃)

EXAMPLE 4 Methyl2-{2-[3-methoximinobut-(E)1-enyl]-phenyl}-3-methoxyprop-(E)2-enoate(compound No. 22 from Table VI)

4.0 g (15 mmol) of methyl2-{2-[3-oxobut-(E)1-enyl]-phenyl}-3-methoxyprop-(E)2-enoate (Example 3)and 1.3 g (15 mmol) of methoxyamine hydrochloride in 100 ml of methanolare refluxed for 1 hour. The mixture is cooled, after which the methanolis stripped off, the residue is taken up in diethyl ether and thesolution is washed with water, dried over magnesium sulfate andevaporated down. The title compound is purified by column chromatography(95:5 cyclohexane/ethyl acetate) and is separated into its C═N doublebond isomers (less polar: anti-oxime ether, oil, 1.4 g; more polar:synoxime ether, oil, 0.5 g; together 1.9 g/44%).

(m, together 3H) and 7.67 (d, 1H; aromatic protons); 7.60 (s, 1H,CH--OCH₃)

EXAMPLE 5 Methyl 2-methoximino-2-{2-[3-oxobut-(E)1-enyl]-phenyl}-acetate(compound No. 78 from Table I)

50 g (226 mmol) of methyl 2-methoximino-2-(2-formylphenyl)-acetate(European Patent 393,428, page 3) and 72 g (227 mmol) oftriphenylphosphoranylideneacetone in 1000 ml of toluene are stirredunder nitrogen for 5 hours at 65° C. The mixture is allowed to cool, thesolvent is stripped off in a rotary evaporator and the title compound(46.9 g/80%) is obtained as yellowish crystals of melting point115°-117° C. by recrystallization from isopropanol.

¹ H-NMR (CDCl₃, d scale): 2.35 (s, 3H, CH₃ --C═O); 3.92 and 4.04 (2 s,each 3H, COOCH₃ and NOCH₃); 6.69 (d, 1H, CH═CH--C═O); 7.26 (mc, 1H),7.47 (mc, 2H) and 7.75 (mc, 1H; aromatic protons); 7.31 (d, 1H,CH═CH--C═O)

EXAMPLE 6 Methyl2-methoximino-2-{2-[3-hydroxyiminobut-(E)1-enyl]-phenyl}-acetate(compound No. 71 from Table VI)

10.4 g (40 mmol) of methyl2-methoximino-2-{2-[3-oxobut-(E)1-enyl]-phenyl}-acetate (Example 5) and3.1 g (44 mmol) of hydroxylamine hydrochloride in 200 ml of methanol arerefluxed for 1 hour. After cooling, the reaction mixture is evaporateddown, the residue is digested in diethyl ether and the solid is filteredoff under suction. Column chromatography gives the title compound asseparate C═N double bond isomers (less polar: syn-oxime, 2.5 g,colorless crystals, mp. 127°-130° C.; more polar: anti-oxime, 5.0 g, mp.136°-138° C.; together 7.5 g/68%).

¹ H-NMR (CDCl₃, d scale): syn-isomer, 2.07 (s, 3H, CH₃ --C═N); 3.98 and4.06 (2 s, each 3H, COOCH₃ and NOCH₃); 6.72 (d, 1H, CH═CH--C═N); 7.00(mc, 1H), 7.3-7.5 (m, 2H) and 7.80 (mc, 1H; aromatic protons), 7.54 (d,1H, CH═CH--C═N); 8.45 (br, 1H, N--OH)/anti-isomer, 2.08 (s, 3 H, CH₃--C═N); 3.90 and 4.05 (2 s, each 3H, COOCH₃ and NOCH₃); 6.73 (d, 1H,CH═CH--C═N; 7.20 (mc, 1H), 7.43 (mc, 2H) and 7.79 (mc, 1H; aromaticprotons), 7.53 (d, 1H, CH═CH--C═N); 8.45 (br, 1H, N--OH)

EXAMPLE 7 Methyl2-methoximino-2-{2-[3-anti-2,6-difluorobenzyl-oximinobut-(E)1-enyl]-phenyl}-acetate(compound No. 107 from Table VII)

0.9 g (15.2 mmol) of powdered potassium hydroxide is added to 4.0 g(15.2 mmol) of methyl2-methoximino-2-{2-[3-anti-hydroximinobut-(E)1-enyl]-phenyl}-acetate(Example 6) in 60 ml of dimethylformamide at +5° C. and a solution of3.1 g (15.2 mmol) of 2,6-difluorobenzyl bromide in 20 ml ofdimethylformamide is added dropwise at this temperature. Stirring iscarried out for a further hour at +5° C. and the reaction mixture ispoured into ice water, extracted 3 times with diethyl ether, dried overmagnesium sulfate and evaporated down. Chromatography (9:1cyclohexane/ethyl acetate, KG 60) gives the title compound (1.2 g/20%)as colorless crystals of melting point 120°-122° C. ¹ H-NMR (CDCl₃, dscale): 1.98 (s, 3H, CH₃ --C═N); 3.87 and 4.01 (2 s, each 3H, COOCH₃ andNOCH₃ ; 5.24 (s, 2H, Ar--CH₂ --O); 6.60 and 6.80 (2 d, each 1H,CH--CH═C═N); 6.93 (mc, 2H), 7.1-7.5 (m, 6H) and 7.70 (mc, 1H; aromaticprotons)

EXAMPLE 8 Methyl2-methoximino-2-{2-[3-benzyloximinobut-(E)1-enyl]-phenyl}-acetate(compound No. 83 from Table VI)

2.0 g (7.6 mmol) of methyl2-methoximino-2-{2-[3-oxobut-(E)1-enyl]-phenyl}-acetate (Example 5) and1.2 g (7.6 mmol) of benzyloxyamine are dissolved in 60 ml of methanol, 1ml of concentrated hydrochloric acid is added and the reaction mixtureis refluxed for 1 hour. It is allowed to cool and is evaporated down,the residue is taken up in diethyl ether, the solution is washed withwater and dried over magnesium sulfate and the solvent is stripped off.Column chromatography (from 95:5 to 90:10 cyclohexane/ethyl acetate)gives the title compound as separate C═N double bond isomers (lesspolar: anti-oxime ether, 1.1 g, oil; more polar: syn-oxime ether, 0.6 g,oil; together 1.7 g/61%).

¹ H-NMR (CDCl₃, d scale): anti-isomer: 2.04 (s, 3H, CH₃ --C═N); 3.88 and4.03 (2 s, each 3H, COOCH₃ and NOCH₃); 5.24 (s, 2H, Ar--CH₂ --O); 6.62and 6.82 (2 d, each 1H, CH═CH--C═N); 7.17 (mc, 1H), 7.3-7.5 (m, 7H) and7.69 (mc, 1H; aromatic protons)

EXAMPLE 9 Methyl2-methoximino-2-{2-[3-anti-phenylhydrazonobut-(E)1-enyl]-phenyl}-acetate(compound No. 68 from Table VII)

2.6 g (10 mmol) of methyl2-methoximino-2-{2-[3-oxobut-(E)1-enyl]-phenyl}-acetate (Example 5) and1.08 g (10 mmol) of phenylhydrazine in 50 ml of methanol are refluxedfor 4 hours. The mixture is allowed to cool, the solvent is stripped offand the product is purified by column chromatography (80:20cyclohexane/ethyl acetate, KG 60). The anti-hydrazone (oil, 1.5 g/43%)is obtained as the only defined product in the form of yellow crystalsfrom diethyl ether (mp. 155°-158° C.).

¹ H-NMR (CDCl₃, d scale): 1.99 (s, 3H, CH₃ --C═N); 3.86 and 4.05 (2 s,each 3H, COOCH₃ and NOCH₃); 6.48 (d, 1H, CH═CH--C═N); 6.86 (t, 1H),7.1-7.5 (m, 7H) and 7.74 (d, 1H; aromatic protons); 7.02 (d, 1H,CH═CH--C═N)

EXAMPLE 10 Methyl2-methoximino-2-{2-[3-oxo-3-(4-methoxyphenyl)prop-(E)1-enyl]-phenyl}-acetate(compound No. 57 from Table II)

7.7 g (35 mmol) of Methyl 2-methoximino-2-(2-formylphenyl)-acetate(European Patent 393,428, page 3) and 15.5 g (38 mmol) oftriphenylphosphoranylidene-4-methoxyacetophenone in 300 ml of tolueneare refluxed for 2 hours. The mixture is cooled and then evaporated downand the residue is subjected to column chromatography (from 95:5 to85:15 cyclohexane/ethyl acetate, KG 60). The title compound (9.7 g/69%)is obtained as virtually colorless crystals (mp. 137°-141° C.).

¹ H-NMR (CDCl, d scale): 3.86, 3.91 and 4.10 (3 s, each 3H, COOCH₃,NOCH₃ and Ar--OCH₃); 7.00 and 8.02 (2 d, each 2H, protons inp-disubstituted aromatics); 7.2-7.9 (m, 6H, protons in o-disubstitutedaromatics and CH═CH--C═O)

EXAMPLE 11 Methyl2-methoximino-2-{2-[3-methoximino-3-(4-methoxyphenyl)-prop-(E)1-enyl]-phenyl}-acetate(compound No. 97 from Table VI)

3.5 g (10 mmol) of methyl2-methoximino-2-{2-[3-oxo-3-(4-methoxyphenyl)-prop-(E)1-enyl]-phenyl}-acetate(Example 10) and 1.0 g (12 mmol) of methoxyamine hydrochloride arerefluxed for 2 hours. The mixture is allowed to reach room temperature(20° C., RT) and the methanol is stripped off. Column chromatography(9:1 cyclohexane/ethyl acetate, KG 60) is the title compound (anti/synisomer mixture, 0.9 g/24%) as a brownish oil which can be crystallizedfrom pentane/diethyl ether (mp. 100°-104° C.).

¹ H-NMR (CDCl₃, d scale): 3.80, 3.82, 3.94 and 4.01 (4 s, each 3H,COOCH₃, both NOCH₃ and Ar--OCH₃ in anti-isomer); 3.78, 3.83, 3.90 and3.92 (4 s, each 3H, COOCH₃, both NOCH₃ and Ar--OCH₃ in syn-isomer); 6.30(d, 1H, CH═CH--C═N in syn-isomer); 6.60 (d, 1H, CH═CH--C═N inanti-isomer); 6.85-7.9 (m, 9H, aromatic protons and CH═CH--C═N in bothisomers)

EXAMPLE 12 Methyl2-methoximino-2-{2-[2-tert-butoxycarbonyl-(E)-ethenyl]-phenyl}-acetate(compound No. 112 from Table I)

17.6 g (80 mmol) of methyl 2-methoximino-2-(2-formylphenyl)-acetate(European Patent 393,428, page 3) and 33 g (88 mmol) of tert-butyltriphenylphosphoranylideneacetate in 500 ml of toluene are stirred undernitrogen for 1 hour at 60° C. The mixture is allowed to cool, thesolvent is stripped off, diethyl ether is added to the residue and themixture is placed in an ice bath. The major amount of triphenylphosphineoxide separates out and is filtered off under suction. The filtrate isevaporated down and the residue is purified by column chromatography(from 95:5 to 93:7 cyclohexane/ethyl acetate). The title compound (24g/94%) is obtained as a brownish oil.

¹ H-NMR (CDCl₃, d scale): 1.53 (s, 9H, (CH₃)₃ CO); 3.85 and 4.03 (2 s,each 3H, COOCH₃ and NOCH₃); 6.33 (d, 1H, CH═CH--C═O); 7.1-7.75 (m, 5H,aromatic protons and CH═CH--C═O)

EXAMPLE 13 Methyl2-methoximino-2-{2-[2-carboxyl-(E)ethenyl]-phenyl}-acetate (compound No.109 from Table I)

A solution of 18 g (48 mmol) of methyl2-methoximino-2-{2-[2-tert-butoxycarbonyl-(E)ethenyl]phenyl}-acetate(Example 12) in 100 ml of THF is stirred with 20 ml of concentratedhydrochloric acid for 45 minutes at 65° C. The mixture is allowed tocool, the solvent is stripped off, the remaining crystal slurry istriturated with diisopropyl ether/pentane and the solid is filtered offunder suction and dried. The title compound (12 g/81%) is obtained asbeige crystals (mp. 178°-182° C.).

¹ H-NMR (CDCl₃, d scale): 3.93 and 4.09 (2 s, each 3H, COOCH₃ andNOCH₃); 6.48, d, 1H, CH═CH--C═O); 7.23 (mc, 1H), 7.50 (mc, 2H) and 7.78(mc, 1H; aromatic protons); 7.59 (d, 1H, CH═CH--C═O); 10.8 (broad, 1H,COOH)

EXAMPLE 14 Methyl2-methoximino-2-{2-[2-(2,6-difluorobenzyloxy-carbonyl-(E)ethenyl]-phenyl}-acetate(compound No. 37 from Table III)

3.4 g (13 mmol) of methyl2-methoximino-2-{2-[2-carboxyl-(E)ethenyl]-phenyl}-acetate (Example 13)are dissolved in 50 ml of dimethylformamide, the solution is cooled to+5° C. and 0.75 g (13 mmol) of powdered potassium hydroxide is added. Asolution of 2.7 g (13 mmol) of 2,6-difluorobenzyl bromide in 15 ml ofdimethylformamide is added dropwise at the same temperature, after whichthe reaction mixture is allowed to reach room temperature and is stirredfor a further hour. The reaction mixture is stirred into ice water andextracted 3 times with diethyl ether and the combined extracts arewashed with water, dried and evaporated down. Trituration of the oilyresidue with diisopropyl ether gives the title compound (3.2 g/63%) incrystalline form (mp. 108°-110° C.).

¹ H-NMR (CDCl₃, d scale): 3.91 and 4.06 (2 s, each 3H, COOCH₃ andNOCH₃); 5.31 (s, 2H, Ar--CH₂ --O); 6.42 (d, 1H, CH═CH--C═O); 6.95 (mc,2H) and 7.1-7.8 (m, 6H; aromatic protons and CH═CH--C═O)

EXAMPLE 15 Methyl2-methoximino-2-{2-[3-oxo-3-phenyl)propyl]-phenyl}-acetate (compound No.50 from Table X)

5.0 g (17.5 mmol) of methyl2-methoximino-2-(2-bromomethylphenyl)-acetate (European Patent 363,818,page 3) and 3.9 g (17.5 mmol) of dibenzoylmethane are dissolved in 50 mlof methanol, and 2.7 g (19.3 mmol) of potassium carbonate and a pinch ofpotassium iodide are added. Stirring is carried out for 90 minutes underreflux, the mixture is allowed to cool and the solvent is stripped off.Water is added to the residue, the latter is extracted twice withmethylene chloride and the combined extracts are dried over magnesiumsulfate and evaporated down. Flash chromatography (from 90:10 to 75:25n-hexane/ethyl acetate) gives the title compound (1.4 g/25%) as a deepred oil.

IR (KBr, ˜, in cm⁻¹): 1722, 1689, 1218, 1205, 1067, 1049, 1015, 957,748, 689

Examples of compounds preferred because of their action as pesticidesare shown in the Tables below.

The double bond C═X in the Tables below has an E (or anti)configuration, unless stated otherwise, and has a double bond betweenthe carbon atoms substituted by R¹ and R² in the general formula I. Ifonly one stereoisomer was isolated in the compounds having a C═N doublebond in the side chain (ie. Z═N--R⁶, N--OR⁷ or N--NR⁸ R⁹), or if theisomers were separated, the configuration is specified in a columnheaded Isomer by the letters a (for anti) and s (for syn). Mixtures ofthe two forms which have not been separated appear in this column aspercentages: a(70) and s(30) means a mixture of 70% of anti-isomer and30% of syn-isomer.

The chemical shift (solvent CDCl₃, standard TMS, δ scale) of protonscorresponding to R¹ and R² was used for characterizing compoundsobtained in noncrystalline form.

                                      TABLE I                                     __________________________________________________________________________     ##STR11##                                                                                                   m.p.                                           No.                                                                              A               R.sup.1                                                                          R.sup.2                                                                          X     (°C.)                                                                       δ (CC .sub.-- H)                    __________________________________________________________________________     1 H               H  H  CHOCH.sub.3                                           2 CH.sub.3        H  H  CHOCH.sub.3                                                                         69-71                                           3 C.sub.2 H.sub.5 H  H  CHOCH.sub.3                                           4 i-C.sub.3 H.sub.7                                                                             H  H  CHOCH.sub.3                                           5 n-C.sub.4 H.sub.9                                                                             H  H  CHOCH.sub.3                                           6 t-C.sub.4 H.sub.9                                                                             H  H  CHOCH.sub.3                                                                         oil  7.07/7.67                                  7 H.sub.2 CCH     H  H  CHOCH.sub.3                                           8 CH.sub.3 CC     H  H  CHOCH.sub.3                                           9 Cyclopropyl     H  H  CHOCH.sub.3                                           10                                                                              Cyclohexyl      H  H  CHOCH.sub.3                                           11                                                                              N-Methylpiperidin-2-yl                                                                        H  H  CHOCH.sub.3                                           12                                                                              C.sub.6 H.sub. 5                                                                              H  H  CHOCH.sub.3                                                                         oil                                             13                                                                              α-Naphthyl                                                                              H  H  CHOCH.sub.3                                           14                                                                              β-Naphthyl H  H  CHOCH.sub.3                                           15                                                                              2-Pyridyl       H  H  CHOCH.sub.3                                           16                                                                              3-Pyridyl       H  H  CHOCH.sub.3                                           17                                                                              4-Pyridyl       H  H  CHOCH.sub.3                                           18                                                                              6-Chloro-2-pyridyl                                                                            H  H  CHOCH.sub.3                                           19                                                                              2-Pyrazinyl     H  H  CHOCH.sub.3                                           20                                                                              2-Quinolinyl    H  H  CHOCH.sub.3                                           21                                                                              2-Furyl         H  H  CHOCH.sub.3                                           22                                                                              3-Thienyl       H  H  CHOCH.sub.3                                           23                                                                              N-Methyl-3-Pyrryl                                                                             H  H  CHOCH.sub.3                                           24                                                                              N-Methyl-2-Indolyl                                                                            H  H  CHOCH.sub.3                                           25                                                                              C.sub.6 H.sub.5 CH.sub.2                                                                      H  H  CHOCH.sub.3                                           26                                                                              β-Naphthylmethyl                                                                         H  H  CHOCH.sub.3                                           27                                                                              2-Pyridylmethyl H  H  CHOCH.sub.3                                           28                                                                              2-Furylmethyl   H  H  CHOCH.sub.3                                           29                                                                              3-Indolylmethyl H  H  CHOCH.sub.3                                           30                                                                              C.sub.6 H.sub.5 CHCH                                                                          H  H  CHOCH.sub.3                                           31                                                                              2-(2-Furyl)ethenyl                                                                            H  H  CHOCH.sub.3                                           32                                                                              CF.sub.2        H  H  CHOCH.sub.3                                           33                                                                              HO              H  H  CHOCH.sub.3                                                                         140-143                                         34                                                                              CH.sub.3 O      H  H  CHOCH.sub.3                                           35                                                                              C.sub.2 H.sub.5 O                                                                             H  H  CHOCH.sub.3                                           36                                                                              t-C.sub.4 H.sub.9 O                                                                           H  H  CHOCH.sub.3                                                                         oil  6.30/7.58                                  37                                                                              H.sub.2 CCHCH.sub.2 O                                                                         H  H  CHOCH.sub.3                                                                         oil  6.44/7.72                                  38                                                                              C.sub.6 H.sub.5 O                                                                             H  H  CHOCH.sub.3                                                                         103-104                                         39                                                                              C.sub.6 H.sub.5 CH.sub.2 O                                                                    H  H  CHOCH.sub.3                                                                         111-112                                         40                                                                              (CH.sub.3).sub.3 SiO                                                                          H  H  CHOCH.sub.3                                           41                                                                              t-C.sub.4 H.sub.9(CH.sub.3).sub.2 SiO                                                         H  H  CHOCH.sub.3                                           42                                                                              H.sub.2 N       H  H  CHOCH.sub.3                                           43                                                                              CH.sub.3 NH     H  H  CHOCH.sub.3                                           44                                                                              (CH.sub.3).sub.2 N                                                                            H  H  CHOCH.sub.3                                           45                                                                              C.sub.6 H.sub.5 NH                                                                            H  H  CHOCH.sub.3                                                                         155                                                                           (oil)                                           46                                                                              C.sub.6 H.sub.5 NCH.sub.3                                                                     H  H  CHOCH.sub.3                                           47                                                                              C.sub.6 H.sub.5 CH.sub.2 NH                                                                   H  H  CHOCH.sub.3                                           48                                                                              2-CH.sub.3 C.sub.6 H.sub.4 CH.sub.2 NH                                                        H  H  CHOCH.sub.3                                           49                                                                              2-ClC.sub.6 H.sub.4 CH.sub.2 NH                                                               H  H  CHOCH.sub.3                                           50                                                                              3-CH.sub.3 OC.sub.6 H.sub.4 CH.sub.2 NH                                                       H  H  CHOCH.sub.3                                           51                                                                              4-Cyano-C.sub.6 H.sub.4CH.sub.2 NH                                                            H  H  CHOCH.sub.3                                            52                                                                             2,6-F.sub.2C.sub.6 H.sub.3CH.sub.2 NH                                                         H  H  CHOCH.sub.3                                           53                                                                              C.sub.6 H.sub.5 CH.sub.2 NCH.sub.3                                                            H  H  CHOCH.sub.3                                                                         122-124                                         54                                                                              2-CH.sub.3 C.sub.6 H.sub.4 CH.sub.2 NCH.sub.3                                                 H  H  CHOCH.sub.3                                           55                                                                              2-ClC.sub.6 H.sub.4 CH.sub.2 NCH.sub.3                                                        H  H  CHOCH.sub.3                                           56                                                                              3-CH.sub.3 OC.sub.6 H.sub.4 CH.sub.2 NCH.sub.3                                                H  H  CHOCH.sub.3                                           57                                                                              4-Cyano-C.sub.6 H.sub.4 CH.sub.2 NCH.sub.3                                                    H  H  CHOCH.sub.3                                           58                                                                              N-Morpholinyl   H  H  CHOCH.sub.3                                                                         149-152                                         59                                                                              HS              H  H  CHOCH.sub.3                                           60                                                                              C.sub.6 H.sub.5 CH.sub.2 S                                                                    H  H  CHOCH.sub.3                                           61                                                                              CH.sub.3        CH.sub.3                                                                         H  CHOCH.sub.3                                           62                                                                              C.sub.6 H.sub.5 CH.sub.3                                                                         H  CHOCH.sub.3                                           63                                                                              t-C.sub.4 H.sub.9 O                                                                           CH.sub.3                                                                         H  CHOCH.sub.3                                           64                                                                              C.sub.6 H.sub.5 CH.sub.2 O                                                                    CH.sub.3                                                                         H  CHOCH.sub.3                                           65                                                                              CH.sub.3 NH     CH.sub.3                                                                         H  CHOCH.sub.3                                           66                                                                              C.sub.6 H.sub.5 NCH.sub.3                                                                     CH.sub.3                                                                         H  CHOCH.sub.3                                           67                                                                              C.sub.6 H.sub.5 CH.sub.2 NCH.sub.3                                                            CH.sub.3                                                                         H  CHOCH.sub.3                                           68                                                                              C.sub.6 H.sub.5 CH.sub.2 S                                                                    CH.sub.3                                                                         H  CHOCH.sub.3                                           69                                                                              CH.sub.3        H  CH.sub.3                                                                         CHOCH.sub.3                                                                         77-79                                           70                                                                              C.sub.6 H.sub.5 H  CH.sub.3                                                                         CHOCH.sub.3                                           71                                                                              t-C.sub.4 H.sub.9 O                                                                           H  CH.sub.3                                                                         CHOCH.sub.3                                                                         oil  7.46                                       72                                                                              C.sub.6 H.sub.5 CH.sub.2 O                                                                    H  CH.sub.3                                                                         CHOCH.sub.3                                           73                                                                              CH.sub.3 NH     H  CH.sub.3                                                                         CHOCH.sub.3                                           74                                                                              C.sub.6 H.sub.5 NCH.sub.3                                                                     H  CH.sub.3                                                                         CHOCH.sub.3                                           75                                                                              C.sub.6 H.sub.5 CH.sub.2 NCH.sub.3                                                            H  CH.sub.3                                                                         CHOCH.sub.3                                           76                                                                              C.sub.6 H.sub.5 CH.sub.2 S                                                                    H  CH.sub.3                                                                         CHOCH.sub.3                                           77                                                                              H               H  H  NOCH.sub.3                                                                          90-94                                           78                                                                              CH.sub.3        H  H  NOCH.sub.3                                                                          115-117                                         79                                                                              C.sub.2 H.sub.5 H  H  NOCH.sub.3                                            80                                                                              i-C.sub.3 H.sub.7                                                                             H  H  NOCH.sub.3                                            81                                                                              n-C.sub.4 H.sub.9                                                                             H  H  NOCH.sub.3                                            82                                                                              t-C.sub.4 H.sub.9                                                                             H  H  NOCH.sub.3                                                                          67-69                                           83                                                                              H.sub.2 CCH     H  H  NOCH.sub.3                                            84                                                                              CH.sub.3 C C    H  H  NOCH.sub.3                                            85                                                                              Cyclopropyl     H  H  NOCH.sub.3                                            86                                                                              Cyclohexyl      H  H  NOCH.sub.3                                            87                                                                              N-Methylpiperidin-2-yl                                                                        H  H  NOCH.sub.3                                            88                                                                              C.sub.6 H.sub.5 H  H  NOCH.sub.3                                                                           98-102                                         89                                                                              α-Naphthyl                                                                              H  H  NOCH.sub.3                                            90                                                                              β-Naphthyl H  H  NOCH.sub.3                                            91                                                                              2-Pyridyl       H  H  NOCH.sub.3                                            92                                                                              3-Pyridyl       H  H  NOCH.sub.3                                            93                                                                              4-Pyridyl       H  H  NOCH.sub.3                                            94                                                                              6-Chloro-2-pyridyl                                                                            H  H  NOCH.sub.3                                            95                                                                              2-Pyrazinyl     H  H  NOCH.sub.3                                            96                                                                              2-Quinolinyl    H  H  NOCH.sub.3                                            97                                                                              2-Furyl         H  H  NOCH.sub.3                                            98                                                                              3-Thienyl       H  H  NOCH.sub.3                                            99                                                                              N-Methyl-3-Pyrryl                                                                             H  H  NOCH.sub.3                                           100                                                                              N-Methyl-2-Indolyl                                                                            H  H  NOCH.sub.3                                           101                                                                              C.sub.6 H.sub.5 CH.sub.2                                                                      H  H  NOCH.sub.3                                           102                                                                              β-Naphthylmethyl                                                                         H  H  NOCH.sub.3                                           103                                                                              2-Pyridylmethyl H  H  NOCH.sub.3                                           104                                                                              2-Furylmethyl   H  H  NOCH.sub.3                                           105                                                                              3-Indolylmethyl H  H  NOCH.sub.3                                           106                                                                              C.sub.6 H.sub.5 CHCH                                                                          H  H  NOCH.sub.3                                           107                                                                              2-(2-Furyl)ethenyl                                                                            H  H  NOCH.sub.3                                           108                                                                              CF.sub.3        H  H  NOCH.sub.3                                           109                                                                              HO              H  H  NOCH.sub.3                                                                          178-182                                        110                                                                              CH.sub.3 O      H  H  NOCH.sub.3                                                                          oil  6.40/7.10                                 111                                                                              C.sub.2 H.sub.5 O                                                                             H  H  NOCH.sub.3                                           112                                                                              t-C.sub.4 H.sub.9 O                                                                           H  H  NOCH.sub.3                                                                          oil  6.33/7.39                                 113                                                                              H.sub.2 CCHCH.sub.2 O                                                                         H  H  NOCH.sub.3                                                                          oil  6.45/7.52                                 114                                                                              C.sub.6 H.sub.5 O                                                                             H  H  NOCH.sub.3                                                                          110                                            115                                                                              C.sub.6 H.sub.5 CH.sub.2 O                                                                    H  H  NOCH.sub.3                                                                          oil  6.49/7.54                                 116                                                                              (CH.sub.3).sub.3 SiO                                                                          H  H  NOCH.sub.3                                           117                                                                              t-C.sub.4 H.sub.9(CH.sub.3).sub.2 SiO                                                         H  H  NOCH.sub.3                                           118                                                                              H.sub.2 N       H  H  NOCH.sub.3                                           119                                                                              CH.sub.3 NH     H  H  NOCH.sub.3                                           120                                                                              (CH.sub.3).sub.2 N                                                                            H  H  NOCH.sub.3                                           121                                                                              C.sub.6 H.sub.5 NH                                                                            H  H  NOCH.sub.3                                                                          115-117                                        112                                                                              C.sub.6 H.sub.5 NCH.sub.3                                                                     H  H  NOCH.sub.3                                                                          136-138                                        123                                                                              C.sub.6 H.sub.5 CH.sub.2 NH                                                                   H  H  NOCH.sub.3                                                                          107-110                                        124                                                                              2-CH.sub.3 C.sub.6 H.sub.4 CH.sub.2 NH                                                        H  H  NOCH.sub.3                                           125                                                                              2-ClC.sub.6 H.sub.4 CH.sub.2 NH                                                               H  H  NOCH.sub.3                                           126                                                                              3-CH.sub.3 OC.sub.6 H.sub.4 CH.sub.2 NH                                                       H  H  NOCH.sub.3                                           127                                                                              4-Cyano-C.sub.6 H.sub.4CH.sub.2 NH                                                            H  H  NOCH.sub.3                                           128                                                                              2,6-F.sub.2C.sub.6 H.sub.3CH.sub.2 NH                                                         H  H  NOCH.sub.3                                           129                                                                              C.sub.6 H.sub.5 CH.sub.2 NCH.sub.3                                                            H  H  NOCH.sub.3                                                                           98-101                                        130                                                                              2-CH.sub.3 C.sub.6 H.sub.4 CH.sub.2 NCH.sub.3                                                 H  H  NOCH.sub.3                                           131                                                                              2-ClC.sub.6 H.sub.4 CH.sub.2 NCH.sub.3                                                        H  H  NOCH.sub.3                                           132                                                                              3-CH.sub.3 OC.sub.6 H.sub.4 CH.sub.2 NCH.sub.3                                                H  H  NOCH.sub.3                                           133                                                                              4-Cyano-C.sub.6 H.sub.4 CH.sub.2 NCH.sub.3                                                    H  H  NOCH.sub.3                                           134                                                                              N-Morpholinyl   H  H  NOCH.sub.3                                                                          132-134                                        135                                                                              HS              H  H  NOCH.sub.3                                           136                                                                              C.sub.6 H.sub.5 CH.sub.2 S                                                                    H  H  NOCH.sub.3                                           137                                                                              CH.sub.3        CH.sub.3                                                                         H  NOCH.sub.3                                           138                                                                              C.sub.6 H.sub.5 CH.sub.3                                                                         H  NOCH.sub.3                                           139                                                                              t-C.sub.4 H.sub.9 O                                                                           CH.sub.3                                                                         H  NOCH.sub.3                                           140                                                                              C.sub.6 H.sub.5 CH.sub.2 O                                                                    CH.sub.3                                                                         H  NOCH.sub.3                                           141                                                                              CH.sub.3 NH     CH.sub.3                                                                         H  NOCH.sub.3                                           142                                                                              C.sub.6 H.sub.5 NCH.sub.3                                                                     CH.sub.3                                                                         H  NOCH.sub.3                                           143                                                                              C.sub.6 H.sub.5 CH.sub.2 NCH.sub.3                                                            CH.sub.3                                                                         H  NOCH.sub.3                                           144                                                                              C.sub.6 H.sub.5 CH.sub.2 S                                                                    CH.sub. 3                                                                        H  NOCH.sub.3                                           145                                                                              CH.sub.3        H  CH.sub.3                                                                         NOCH.sub.3                                                                          oil  7.33                                      146                                                                              C.sub.6 H.sub.5 H  CH.sub.3                                                                         NOCH.sub.3                                           147                                                                              t-C.sub.4 H.sub.9 O                                                                           H  CH.sub.3                                                                         NOCH.sub.3                                                                          oil  7.28                                      148                                                                              C.sub.6 H.sub.5 CH.sub.2 O                                                                    H  CH.sub.3                                                                         NOCH.sub.3                                           149                                                                              CH.sub.3 NH     H  CH.sub.3                                                                         NOCH.sub.3                                           150                                                                              C.sub.6 H.sub.5 NCH.sub.3                                                                     H  CH.sub.3                                                                         NOCH.sub.3                                           151                                                                              C.sub.6 H.sub.5 CH.sub.2 NCH.sub.3                                                            H  CH.sub.3                                                                         NOCH.sub.3                                           152                                                                              C.sub.6 H.sub.5 CH.sub.2 S                                                                    H  CH.sub.3                                                                         NOCH.sub.3                                           153                                                                              H               H  H  CHCH.sub.3                                           154                                                                              CH.sub.3        H  H  CHCH.sub.3                                           155                                                                              C.sub.2 H.sub.5 H  H  CHCH.sub.3                                           156                                                                              i-C.sub.3 H.sub.7                                                                             H  H  CHCH.sub.3                                           157                                                                              n-C.sub.4 H.sub.9                                                                             H  H  CHCH.sub.3                                           158                                                                              t-C.sub.4 H.sub.9                                                                             H  H  CHCH.sub.3                                           159                                                                              H.sub.2 CCH     H  H  CHCH.sub.3                                           160                                                                              CH.sub.3 CC     H  H  CHCH.sub.3                                           161                                                                              Cyclopropyl     H  H  CHCH.sub.3                                           162                                                                              Cyclohexyl      H  H  CHCH.sub.3                                           163                                                                              N-Methylpiperidin-2-yl                                                                        H  H  CHCH.sub.3                                           164                                                                              C.sub.6 H.sub.5 H  H  CHCH.sub.3                                           165                                                                              α-Naphthyl                                                                              H  H  CHCH.sub.3                                           166                                                                              β-Naphthyl H  H  CHCH.sub.3                                           167                                                                              2-Pyridyl       H  H  CHCH.sub.3                                           168                                                                              3-Pyridyl       H  H  CHCH.sub.3                                           169                                                                              4-Pyridyl       H  H  CHCH.sub.3                                           170                                                                              6-Chloro-2-pyridyl                                                                            H  H  CHCH.sub.3                                           171                                                                              2-Pyrazinyl     H  H  CHCH.sub.3                                           172                                                                              2-Quinolinyl    H  H  CHCH.sub.3                                           173                                                                              2-Furyl         H  H  CHCH.sub.3                                           174                                                                              3-Thienyl       H  H  CHCH.sub.3                                           175                                                                              N-Methyl-3-pyrryl                                                                             H  H  CHCH.sub.3                                           176                                                                              N-Methyl-2-indolyl                                                                            H  H  CHCH.sub.3                                           177                                                                              C.sub.6 H.sub.5 CH.sub.2                                                                      H  H  CHCH.sub.3                                           178                                                                              β-Naphthylmethyl                                                                         H  H  CHCH.sub.3                                           179                                                                              2-Pyridylmethyl H  H  CHCH.sub.3                                           180                                                                              2-Furylmethyl   H  H  CHCH.sub.3                                           181                                                                              3-Indolylmethyl H  H  CHCH.sub.3                                           182                                                                              C.sub.6 H.sub.5 CHCH                                                                          H  H  CHCH.sub.3                                           183                                                                              2-(2-Furyl)ethenyl                                                                            H  H  CHCH.sub.3                                           184                                                                              CF.sub.3        H  H  CHCH.sub.3                                           185                                                                              HO              H  H  CHCH.sub.3                                           186                                                                              CH.sub.3 O      H  H  CHCH.sub.3                                           187                                                                              C.sub.2 H.sub.5 O                                                                             H  H  CHCH.sub.3                                           188                                                                              t-C.sub.4 H.sub.9 O                                                                           H  H  CHCH.sub.3                                           189                                                                              H.sub.2 CCHCH.sub.2 O                                                                         H  H  CHCH.sub.3                                           190                                                                              C.sub.6 H.sub.5 O                                                                             H  H  CHCH.sub.3                                           191                                                                              C.sub.6 H.sub.5 CH.sub.2 O                                                                    H  H  CHCH.sub. 3                                          192                                                                              (CH.sub.3).sub.3 SiO                                                                          H  H  CHCH.sub.3                                           193                                                                              t-C.sub.4 H.sub.9(CH.sub.3).sub.2 SiO                                                         H  H  CHCH.sub.3                                           194                                                                              H.sub.2 N       H  H  CHCH.sub.3                                           195                                                                              CH.sub.3 NH     H  H  CHCH.sub.3                                           196                                                                              (CH.sub.3).sub.2 N                                                                            H  H  CHCH.sub.3                                           197                                                                              C.sub.6 H.sub.5 NH                                                                            H  H  CHCH.sub.3                                           198                                                                              C.sub.6 H.sub.5 NCH.sub.3                                                                     H  H  CHCH.sub.3                                           199                                                                              C.sub.6 H.sub.5 CH.sub.2 NH                                                                   H  H  CHCH.sub.3                                           200                                                                              2-CH.sub.3 C.sub.6 H.sub.4 CH.sub.2 NH                                                        H  H  CHCH.sub.3                                           201                                                                              2-ClC.sub.6 H.sub.4 CH.sub.2 NH                                                               H  H  CHCH.sub.3                                           202                                                                              3-CH.sub.3 OC.sub.6 H.sub.4 CH.sub.2 NH                                                       H  H  CHCH.sub.3                                           203                                                                              4-Cyano-C.sub.6 H.sub.4CH.sub.2 NH                                                            H  H  CHCH.sub.3                                           204                                                                              2,6-F.sub.2C.sub.6 H.sub.3CH.sub.2 NH                                                         H  H  CHCH.sub.3                                           205                                                                              C.sub.6 H.sub.5 CH.sub.2 NCH.sub.3                                                            H  H  CHCH.sub.3                                           206                                                                              2-CH.sub.3 C.sub.6 H.sub.4 CH.sub.2 NCH.sub.3                                                 H  H  CHCH.sub.3                                           207                                                                              2-ClC.sub.6 H.sub.4 CH.sub.2 NCH.sub.3                                                        H  H  CHCH.sub.3                                           208                                                                              3-CH.sub.3 OC.sub.6 H.sub.4 CH.sub.2 NCH.sub.3                                                H  H  CHCH.sub.3                                           209                                                                              4-Cyano-C.sub.6 H.sub.4 CH.sub.2 NCH.sub.3                                                    H  H  CHCH.sub.3                                           210                                                                              N-Morpholinyl   H  H  CHCH.sub.3                                           211                                                                              HS              H  H  CHCH.sub.3                                           212                                                                              C.sub.6 H.sub.5 CH.sub.2 S                                                                    H  H  CHCH.sub.3                                           213                                                                              CH.sub.3        CH.sub.3                                                                         H  CHCH.sub.3                                           214                                                                              C.sub.6 H.sub.5 CH.sub.3                                                                         H  CHCH.sub.3                                           215                                                                              t-C.sub.4 H.sub.9 O                                                                           CH.sub.3                                                                         H  CHCH.sub.3                                           216                                                                              C.sub.6 H.sub.5 CH.sub.2 O                                                                    CH.sub.3                                                                         H  CHCH.sub.3                                           217                                                                              CH.sub.3 NH     CH.sub.3                                                                         H  CHCH.sub.3                                           218                                                                              C.sub.6 H.sub.5 NCH.sub.3                                                                     CH.sub.3                                                                         H  CHCH.sub.3                                           219                                                                              C.sub.6 H.sub.5 CH.sub.2 NCH.sub.3                                                            CH.sub.3                                                                         H  CHCH.sub.3                                           220                                                                              C.sub.6 H.sub.5 CH.sub.2 S                                                                    CH.sub.3                                                                         H  CHCH.sub.3                                           221                                                                              CH.sub.3        H  CH.sub.3                                                                         CHCH.sub.3                                           222                                                                              C.sub.6 H.sub.5 H  CH.sub.3                                                                         CHCH.sub.3                                           223                                                                              t-C.sub.4 H.sub.9 O                                                                           H  CH.sub.3                                                                         CHCH.sub.3                                           224                                                                              C.sub.6 H.sub.5 CH.sub.2 O                                                                    H  CH.sub.3                                                                         CHCH.sub.3                                           225                                                                              CH.sub.3 NH     H  CH.sub.3                                                                         CHCH.sub.3                                           226                                                                              C.sub.6 H.sub.5 NCH.sub.3                                                                     H  CH.sub.3                                                                         CHCH.sub.3                                           227                                                                              C.sub.6 H.sub.5 CH.sub.2 NCH.sub.3                                                            H  CH.sub.3                                                                         CHCH.sub.3                                           228                                                                              C.sub.6 H.sub.5 CH.sub.2 S                                                                    H  CH.sub.3                                                                         CHCH.sub.3                                           229                                                                              H               H  H  CHC.sub.2 H.sub.5                                    230                                                                              CH.sub.3        H  H  CHC.sub.2 H.sub.5                                    231                                                                              C.sub.2 H.sub.5 H  H  CHC.sub.2 H.sub.5                                    232                                                                              i-C.sub.3 H.sub.7                                                                             H  H  CHC.sub.2 H.sub.5                                    233                                                                              n-C.sub.4 H.sub.9                                                                             H  H  CHC.sub.2 H.sub.5                                    234                                                                              t-C.sub.4 H.sub.9                                                                             H  H  CHC.sub.2 H.sub.5                                    235                                                                              H.sub.2 CCH     H  H  CHC.sub.2 H.sub.5                                    236                                                                              CH.sub.3 CC     H  H  CHC.sub.2 H.sub.5                                    237                                                                              Cyclopropyl     H  H  CHC.sub.2 H.sub.5                                    238                                                                              Cyclohexyl      H  H  CHC.sub.2 H.sub.5                                    239                                                                              N-Methylpiperidin-2-yl                                                                        H  H  CHC.sub.2 H.sub.5                                    240                                                                              C.sub.6 H.sub.5 H  H  CHC.sub.2 H.sub.5                                    241                                                                              α-Naphthyl                                                                              H  H  CHC.sub.2 H.sub.5                                    242                                                                              β-Naphthyl H  H  CHC.sub.2 H.sub.5                                    243                                                                              2-Pyridyl       H  H  CHC.sub.2 H.sub.5                                    244                                                                              3-Pyridyl       H  H  CHC.sub.2 H.sub.5                                    245                                                                              4-Pyridyl       H  H  CHC.sub.2 H.sub.5                                    246                                                                              6-Chloro-2-pyridyl                                                                            H  H  CHC.sub.2 H.sub.5                                    247                                                                              2-Pyrazinyl     H  H  CHC.sub.2 H.sub.5                                    248                                                                              2-Quinolinyl    H  H  CHC.sub.2 H.sub.5                                    249                                                                              2-Furyl         H  H  CHC.sub.2 H.sub.5                                    250                                                                              3-Thienyl       H  H  CHC.sub.2 H.sub.5                                    251                                                                              N-Methyl-3-pyrryl                                                                             H  H  CHC.sub.2 H.sub.5                                    252                                                                              N-Methyl-2-indolyl                                                                            H  H  CHC.sub.2 H.sub.5                                    253                                                                              C.sub.6 H.sub.5 CH.sub.2                                                                      H  H  CHC.sub.2 H.sub.5                                    254                                                                              β-Naphthylmethyl                                                                         H  H  CHC.sub.2 H.sub.5                                    255                                                                              2-Pyridylmethyl H  H  CHC.sub.2 H.sub.5                                    256                                                                              2-Furylmethyl   H  H  CHC.sub.2 H.sub.5                                    257                                                                              3-Indolylmethyl H  H  CHC.sub.2 H.sub.5                                    258                                                                              C.sub.6 H.sub.5 CHCH                                                                          H  H  CHC.sub.2 H.sub.5                                    259                                                                              2-(2-Furyl)ethenyl                                                                            H  H  CHC.sub.2 H.sub.5                                    260                                                                              CF.sub.3        H  H  CHC.sub.2 H.sub.5                                    261                                                                              HO              H  H  CHC.sub.2 H.sub.5                                    262                                                                              CH.sub.3 O      H  H  CHC.sub.2 H.sub.5                                    263                                                                              C.sub.2 H.sub.5 O                                                                             H  H  CHC.sub.2 H.sub.5                                    264                                                                              t-C.sub.4 H.sub.9 O                                                                           H  H  CHC.sub.2 H.sub.5                                    265                                                                              H.sub.2 CCHCH.sub.2 O                                                                         H  H  CHC.sub.2 H.sub.5                                    266                                                                              C.sub.6 H.sub.5 O                                                                             H  H  CHC.sub.2 H.sub.5                                    267                                                                              C.sub.6 H.sub.5 CH.sub.2 O                                                                    H  H  CHC.sub. 2 H.sub.5                                   268                                                                              (CH.sub.3).sub.3 SiO                                                                          H  H  CHC.sub.2 H.sub.5                                    269                                                                              t-C.sub.4 H.sub.9(CH.sub.3).sub.2 SiO                                                         H  H  CHC.sub.2 H.sub.5                                    270                                                                              H.sub.2 N       H  H  CHC.sub.2 H.sub.5                                    271                                                                              CH.sub.3 NH     H  H  CHC.sub.2 H.sub.5                                    272                                                                              (CH.sub.3).sub.2 N                                                                            H  H  CHC.sub.2 H.sub.5                                    273                                                                              C.sub.6 H.sub.5 NH                                                                            H  H  CHC.sub.2 H.sub.5                                    274                                                                              C.sub.6 H.sub.5 NCH.sub.3                                                                     H  H  CHC.sub.2 H.sub.5                                    275                                                                              C.sub.6 H.sub.5 CH.sub.2 NH                                                                   H  H  CHC.sub.2 H.sub.5                                    276                                                                              2-CH.sub.3 C.sub.6 H.sub.4 CH.sub.2 NH                                                        H  H  CHC.sub.2 H.sub.5                                    277                                                                              2-ClC.sub.6 H.sub.4 CH.sub.2 NH                                                               H  H  CHC.sub.2 H.sub.5                                    278                                                                              3-CH.sub.3 OC.sub.6 H.sub.4 CH.sub.2 NH                                                       H  H  CHC.sub.2 H.sub.5                                    279                                                                              4-Cyano-C.sub.6 H.sub.4CH.sub.2 NH                                                            H  H  CHC.sub.2 H.sub.5                                    280                                                                              2,6-F.sub.2C.sub.6 H.sub.3CH.sub.2 NH                                                         H  H  CHC.sub.2 H.sub.5                                    281                                                                              C.sub.6 H.sub.5 CH.sub.2 NCH.sub.3                                                            H  H  CHC.sub.2 H.sub.5                                    282                                                                              2-CH.sub.3 C.sub.6 H.sub.4 CH.sub.2 NCH.sub.3                                                 H  H  CHC.sub.2 H.sub.5                                    283                                                                              2-ClC.sub.6 H.sub.4 CH.sub.2 NCH.sub.3                                                        H  H  CHC.sub.3 H.sub.5                                    284                                                                              3-CH.sub.3 OC.sub.6 H.sub.4 CH.sub.2 NCH.sub.3                                                H  H  CHC.sub.2 H.sub.5                                    285                                                                              4-Cyano-C.sub.6 H.sub.4 CH.sub.2 NCH.sub.3                                                    H  H  CHC.sub.2 H.sub.5                                    286                                                                              N-Morpholinyl   H  H  CHC.sub.2 H.sub.5                                    287                                                                              HS              H  H  CHC.sub.2 H.sub.5                                    288                                                                              C.sub.6 H.sub.5 CH.sub.2 S                                                                    H  H  CHC.sub.2 H.sub.5                                    289                                                                              CH.sub.3        CH.sub.3                                                                         H  CHC.sub.2 H.sub.5                                    290                                                                              C.sub.6 H.sub.5 CH.sub.3                                                                         H  CHC.sub.2 H.sub.5                                    291                                                                              t-C.sub.4 H.sub.9 O                                                                           CH.sub.3                                                                         H  CHC.sub.2 H.sub.5                                    292                                                                              C.sub.6 H.sub.5 CH.sub.2 O                                                                    CH.sub.3                                                                         H  CHC.sub.2 H.sub.5                                    293                                                                              CH.sub.3 NH     CH.sub.3                                                                         H  CHC.sub.2 H.sub.5                                    294                                                                              C.sub.6 H.sub.5 NCH.sub.3                                                                     CH.sub.3                                                                         H  CHC.sub.2 H.sub.5                                    295                                                                              C.sub.6 H.sub.5 CH.sub.2 NCH.sub.3                                                            CH.sub.3                                                                         H  CHC.sub.2 H.sub.5                                    296                                                                              C.sub.6 H.sub.5 CH.sub.2 S                                                                    CH.sub.3                                                                         H  CHC.sub.2 H.sub.5                                    297                                                                              CH.sub.3        H  CH.sub.3                                                                         CHC.sub.2 H.sub.5                                    298                                                                              C.sub.6 H.sub.5 H  CH.sub.3                                                                         CHC.sub.2 H.sub.5                                    299                                                                              t-C.sub.4 H.sub.9 O                                                                           H  CH.sub.3                                                                         CHC.sub.2 H.sub.5                                    300                                                                              C.sub.6 H.sub.5 CH.sub.2 O                                                                    H  CH.sub.3                                                                         CHC.sub.2 H.sub.5                                    301                                                                              CH.sub.3 NH     H  CH.sub.3                                                                         CHC.sub.2 H.sub.5                                    302                                                                              C.sub.6 H.sub.5 NCH.sub.3                                                                     H  CH.sub.3                                                                         CHC.sub.2 H.sub.5                                    303                                                                              C.sub.6 H.sub.5 CH.sub.2 NCH.sub.3                                                            H  CH.sub.3                                                                         CHC.sub.2 H.sub.5                                    304                                                                              C.sub.6 H.sub.5 CH.sub.2 S                                                                    H  CH.sub.3                                                                         CHC.sub.2 H.sub.5                                    305                                                                              2-CH.sub.3C.sub.6 H.sub.4 O                                                                   H  H  CHOCH.sub.3                                                                         oil  6.61/7.89                                 306                                                                              3-CH.sub.3C.sub.6 H.sub.4 O                                                                   H  H  CHOCH.sub.3                                                                         oil  6.60/7.87                                 307                                                                              4-CH.sub.3C.sub.6 H.sub.4 O                                                                   H  H  CHOCH.sub.3                                          308                                                                              3-CF.sub.3C.sub.6 H.sub.4 O                                                                   H  H  CHOCH.sub.3                                                                         oil  6.60/7.88                                 309                                                                              4-ClC.sub.6 H.sub.4 O                                                                         H  H  CHOCH.sub.3                                          310                                                                              4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4 O                                                          H  H  CHOCH.sub.3                                                                         106-107                                        311                                                                              4-CH.sub.3 ONC(CH.sub.3)C.sub.6 H.sub.4 O                                                     H  H  CHOCH.sub.3                                                                         136-138                                        312                                                                              3,4-Cl.sub.2 C.sub.6 H.sub.3 O                                                                H  H  CHOCH.sub.3                                                                         88-90                                          313                                                                              3,5-Cl.sub.2C.sub.6 H.sub.3 O                                                                 H  H  CHOCH.sub.3                                                                         93-95                                          314                                                                              2-Phenyloxazol-4-yl-                                                                          H  H  CHOCH.sub.3                                                                         oil  6.48/7.33                                    methoxy                                                                    315                                                                              CH.sub.3 OOCCH.sub.2 O                                                                        H  H  CHOCH.sub.3                                                                         oil  6.47/7.78                                 316                                                                              t-C.sub.4 H.sub.9 OOCCH.sub.2 O                                                               H  H  CHOCH.sub.3                                                                         oil  6.47/7.76                                 317                                                                              t-C.sub.4 H.sub.9 NH                                                                          H  H  CHOCH.sub.3                                                                         168-169                                        318                                                                              CH.sub.3 OOOCH(CH.sub.3)NH                                                                    H  H  CHOCH.sub.3                                                                         130-133                                        319                                                                              CH.sub.3 OOCCH(i-C.sub.4 H.sub.9)NH                                                           H  H  CHOCH.sub.3                                                                         142-144                                        320                                                                              Piperidin-1-yl  H  H  CHOCH.sub.3                                                                         134-135                                        321                                                                              CH.sub.2C(CH.sub.3)CH.sub.2 ONH                                                               H  H  CHOCH.sub.3                                          322                                                                              CH.sub.2CClCH.sub.2 ONH                                                                       H  H  CHOCH.sub.3                                          323                                                                              3',4'-Cl.sub.2C.sub.6 H.sub.3CH.sub.2 ONH                                                     H  H  CHOCH.sub.3                                                                         112-114                                        324                                                                              HO              H  CH.sub.3                                                                         CHOCH.sub.3                                                                              7.73                                      325                                                                              2-CH.sub.3C.sub.6 H.sub.4 O                                                                   H  CH.sub.3                                                                         CHOCH.sub.3                                          326                                                                              3-CF.sub.3C.sub.6 H.sub.4 O                                                                   H  CH.sub.3                                                                         CHOCH.sub.3                                          327                                                                              4-ClC.sub. 6 H.sub.4 O                                                                        H  CH.sub.3                                                                         CHOCH.sub.3                                          328                                                                              3,5-Cl.sub.2C.sub.6 H.sub.4 O                                                                 H  CH.sub.3                                                                         CHOCH.sub.3                                          329                                                                              2-CH.sub.3C.sub.6 H.sub.4 O                                                                   H  H  NOCH.sub.3                                                                          oil  6.63/7.69                                 330                                                                              3-CH.sub.3C.sub.6 H.sub.4 O                                                                   H  H  NOCH.sub.3                                                                          86-87                                          331                                                                              4-CH.sub.3 C.sub.6 H.sub.4 O                                                                  H  H  NOCH.sub.3                                           332                                                                              3-CF.sub.3C.sub.6 H.sub.4 O                                                                   H  H  NOCH.sub.3                                                                          96-98                                          333                                                                              4-ClC.sub.6 H.sub.4 O                                                                         H  H  NOCH.sub.3                                           334                                                                              4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4 O                                                          H  H  NOCH.sub.3                                                                          139-140                                        335                                                                              4-CH.sub.3 ONC(CH.sub.3)C.sub.6 H.sub.4 O                                                     H  H  NOCH.sub.3                                                                          79-81                                          336                                                                              3,4-Cl.sub.2C.sub.6 H.sub.3 O                                                                 H  H  NOCH.sub.3                                                                          136-138                                        337                                                                              3,5-Cl.sub.2C.sub.6 H.sub.3 O                                                                 H  H  NOCH.sub.3                                                                          115-116                                        338                                                                              2-Phenyloxazol-4-yl-                                                                          H  H  NOCH.sub.3                                                                          134-135                                           methoxy                                                                    339                                                                              CH.sub.3 OOCCH.sub.2 O                                                                        H  H  NOCH.sub.3                                                                          oil  6.50/7.77                                 340                                                                              t-C.sub.4 H.sub.9 OOCCH.sub.2 O                                                               H  H  NOCH.sub.3                                                                          oil  6.48/7.53                                 341                                                                              t-C.sub.4 H.sub.9 NH                                                                          H  H  NOCH.sub.3                                                                          199-202                                        342                                                                              CH.sub.3 OOOCH(CH.sub.3)NH                                                                    H  H  NOCH.sub.3                                           343                                                                              CH.sub.3 OOCCH(i-C.sub.4 H.sub.9)NH                                                           H  H  NOCH.sub.3                                           344                                                                              Piperidin-1-yl  H  H  NOCH.sub.3                                                                          122-124                                        345                                                                              CH.sub.2C(CH.sub.3)CH.sub.2 ONH                                                               H  H  NOCH.sub.3                                                                          133-136                                        346                                                                              CH.sub.2CClCH.sub.2 ONH                                                                       H  H  NOCH.sub.3                                           347                                                                              3',4'-Cl.sub.2C.sub.6 H.sub.3CH.sub.2 ONH                                                     H  H  NOCH.sub.3                                                                          119-120                                        348                                                                              HO              H  CH.sub.3                                                                         NOCH.sub.3                                           349                                                                              2-CH.sub.3C.sub.6 H.sub.4 O                                                                   H  CH.sub.3                                                                         NOCH.sub.3                                           350                                                                              3-CF.sub.3C.sub.6 H.sub.4 O                                                                   H  CH.sub.3                                                                         NOCH.sub.3                                           351                                                                              4-ClC.sub.6 H.sub.4 O                                                                         H  CH.sub.3                                                                         NOCH.sub.3                                           352                                                                              3,5-Cl.sub.2C.sub.6 H.sub.3 O                                                                 H  CH.sub.3                                                                         NOCH.sub.3                                           353                                                                              i-C.sub.3 H.sub.7 O                                                                           H  H  CHOCH.sub.3                                                                         75-76                                          354                                                                              i-C.sub.3 H.sub.7 O                                                                           H  CH.sub.3                                                                         CHOCH.sub.3                                          355                                                                              i-C.sub.3 H.sub.7 O                                                                           H  H  NOCH.sub.3                                           356                                                                              i-C.sub.3 H.sub.7 O                                                                           H  CH.sub.3                                                                         NOCH.sub.3                                           __________________________________________________________________________

                                      TABLE II                                    __________________________________________________________________________     ##STR12##                                                                                                m.p.                                              No. Q.sub.m           X     (°C.)                                                                       δ (CC .sub.--H)                        __________________________________________________________________________    1   3-F               CHOCH.sub.3                                             2   2,6-F.sub.2       CHOCH.sub.3                                             3   2-Cl              CHOCH.sub.3                                             4   3-Cl              CHOCH.sub.3                                             5   4-Cl              CHOCH.sub.3                                             6   2,6-Cl.sub.2      CHOCH.sub.3                                             7   3,4-Cl.sub.2      CHOCH.sub.3                                             8   3-Br              CHOCH.sub.3                                             9   4-I               CHOCH.sub.3                                             10  2-Cl, 6-F         CHOCH.sub.3                                             11  2-CH.sub.3        CHOCH.sub.3                                             12  3-CH.sub.3        CHOCH.sub.3                                             13  4-CH.sub.3        CHOCH.sub.3                                             14  2,4-(CH.sub.3).sub.2                                                                            CHOCH.sub.3                                             15  2,4,6-(CH.sub.3).sub.3                                                                          CHOCH.sub.3                                             16  3-C.sub.2 H.sub.5 CHOCH.sub.3                                             17  R-t-C.sub.4 H.sub.9                                                                             CHOCH.sub.3                                             18  4-Cyclohexyl      CHOCH.sub.3                                             19  3-CH.sub.2 C.sub.6 H.sub.5                                                                      CHOCH.sub.3                                             20  2-OCH.sub.3       CHOCH.sub.3                                             21  3-OCH.sub.3       CHOCH.sub.3                                             22  4-OCH.sub.3       CHOCH.sub.3                                                                         Oil  7.50/                                                                         7.81                                         23  2-O-i-C.sub.3 H.sub.7                                                                           CHOCH.sub.3                                             24  3-OCH.sub.2 C.sub.6 H.sub.5                                                                     CHOCH.sub.3                                             25  3-CF.sub.3        CHOCH.sub.3                                             26  3-NO.sub.2        CHOCH.sub.3                                             27  4-NO.sub.2        CHOCH.sub.3                                             28  3-Cyano           CHOCH.sub.3                                             29  2-Cl, 4-CH.sub.3  CHOCH.sub.3                                             30  2-COOCH.sub.3     CHOCH.sub.3                                             31  4-CH.sub.2 OCH.sub.3                                                                            CHOCH.sub.3                                             32  4-COCH.sub.3      CHOCH.sub.3                                             33  2-CH.sub.3 -4-COCH.sub.3                                                                        CHOCH.sub.3                                             34  4-C(CH.sub.3)NOCH.sub.2 CHCH.sub.2                                                              CHOCH.sub.3                                             35  2-CH.sub.3 -4-C(CH.sub.3)NOCH.sub.2 CHCH.sub.2                                                  CHOCH.sub.3                                             36  3-F               NOCH.sub.3                                              37  2,6-F.sub.2       NOCH.sub.3                                              38  2-Cl              NOCH.sub.3                                              39  3-Cl              NOCH.sub.3                                              40  4-Cl              NOCH.sub.3                                                                          104-107                                           41  2,6-Cl.sub.2      NOCH.sub.3                                              42  3,4-Cl.sub.2      NOCH.sub.3                                              43  3-Br              NOCH.sub.3                                              44  4-I               NOCH.sub.3                                              45  2-Cl, 6-F         NOCH.sub.3                                              46  2-CH.sub.3        NOCH.sub.3                                              47  3-CH.sub.3        NOCH.sub.3                                              48  4-CH.sub.3        NOCH.sub.3                                              49  2,4-(CH.sub.3).sub.2                                                                            NOCH.sub.3                                              50  2,4,6-(CH.sub.3).sub.3                                                                          NOCH.sub.3                                              51  3-C.sub.2 H.sub.5 NOCH.sub.3                                              52  4-t-C.sub.4 H.sub.9                                                                             NOCH.sub.3                                              53  4-Cyclohexyl      NOCH.sub.3                                              54  3-CH.sub.2 C.sub.6 H.sub.5                                                                      NOCH.sub.3                                              55  2-OCH.sub.3       NOCH.sub.3                                              56  3-OCH.sub.3       NOCH.sub.3                                                                           98-102                                           57  4-OCH.sub.3       NOCH.sub.3                                                                          137-141                                           58  2-O-i-C.sub.3 H.sub.7                                                                           NOCH.sub.3                                              59  3-OCH.sub.2 C.sub.6 H.sub.5                                                                     NOCH.sub.3                                              60  3-CF.sub.3        NOCH.sub.3                                              61  3-NO.sub.2        NOCH.sub.3                                              62  4-NO.sub.2        NOCH.sub.3                                              63  3-Cyano           NOCH.sub.3                                              64  2-Cl, 4-CH.sub.3  NOCH.sub.3                                              65  2-COOCH.sub.3     NOCH.sub.3                                              66  4-CH.sub.2 OCH.sub.3                                                                            NOCH.sub.3                                              67  4-COCH.sub.3      NOCH.sub.3                                              68  2-CH.sub.3 -4-COCH.sub.3                                                                        NOCH.sub.3                                              69  4-C(CH.sub.3)NOCH.sub.2 CHCH.sub.2                                                              NOCH.sub.3                                              70  2-CH.sub.3 -4-C(CH.sub.3)NOCH.sub.2 CHCH.sub.2                                                  NOCH.sub.3                                              71  3-F               CHCH.sub.3                                              72  2,6-F.sub.2       CHCH.sub.3                                              73  2-Cl              CHCH.sub.3                                              74  3-Cl              CHCH.sub.3                                              75  4-Cl              CHCH.sub.3                                              76  2,6-Cl.sub.2      CHCH.sub.3                                              77  3,4-Cl.sub.2      CHCH.sub.3                                              78  3-Br              CHCH.sub.3                                              79  R-I               CHCH.sub.3                                              80  2-Cl, 6-F         CHCH.sub.3                                              81  2-CH.sub.3        CHCH.sub.3                                              82  3-CH.sub.3        CHCH.sub.3                                              83  4-CH.sub.3        CHCH.sub.3                                              84  2,4-(CH.sub.3).sub.2                                                                            CHCH.sub.3                                              85  2,4,6-(CH.sub.3).sub.3                                                                          CHCH.sub.3                                              86  3-C.sub.2 H.sub.5 CHCH.sub.3                                              87  4-t-C.sub.4 H.sub.9                                                                             CHCH.sub.3                                              88  4-Cyclohexyl      CHCH.sub.3                                              89  3-CH.sub.2 C.sub.6 H.sub.5                                                                      CHCH.sub.3                                              90  2-OCH.sub.3       CHCH.sub.3                                              91  3-OCH.sub. 3      CHCH.sub.3                                              92  4-OCH.sub.3       CHCH.sub.3                                              93  2-O-i-C.sub.3 H.sub.7                                                                           CHCH.sub.3                                              94  3-OCH.sub.2 C.sub.6 H.sub.5                                                                     CHCH.sub.3                                              95  3-CF.sub.3        CHCH.sub.3                                              96  3-NO.sub.2        CHCH.sub.3                                              97  4-NO.sub.2        CHCH.sub.3                                              98  3-Cyano           CHCH.sub.3                                              99  2-Cl, 4-CH.sub.3  CHCH.sub.3                                              100 2-COOCH.sub.3     CHCH.sub.3                                              101 4-CH.sub.2 OCH.sub.3                                                                            CHCH.sub.3                                              102 4-COCH.sub.3      CHCH.sub.3                                              103 2-CH.sub.3 -4-COCH.sub.3                                                                        CHCH.sub.3                                              104 4-C(CH.sub.3)NOCH.sub.2 CHCH.sub.2                                                              CHCH.sub.3                                              105 2-CH.sub.3 -4-C(CH.sub.3)NOCH.sub.2 CHCH.sub.2                                                  CHCH.sub.3                                              106 3-F               CHC.sub.2 H.sub.5                                       107 2,6-F.sub.2       CHC.sub.2 H.sub.5                                       108 2-Cl              CHC.sub.2 H.sub.5                                       109 3-Cl              CHC.sub.2 H.sub.5                                       110 4-Cl              CHC.sub.2 H.sub.5                                       111 2,6-Cl.sub.2      CHC.sub.2 H.sub.5                                       112 3,4-Cl.sub.2      CHC.sub.2 H.sub.5                                       113 3-Br              CHC.sub.2 H.sub.5                                       114 4-I               CHC.sub.2 H.sub.5                                       115 2-Cl, 6-F         CHC.sub.2 H.sub.5                                       116 2-CH.sub.3        CHC.sub.2 H.sub.5                                       117 3-CH.sub.3        CHC.sub.2 H.sub.5                                       118 4-CH.sub.3        CHC.sub.2 H.sub.5                                       119 2,4-(CH.sub.3).sub.2                                                                            CHC.sub.2 H.sub.5                                       120 2,4,6-(CH.sub.3).sub.3                                                                          CHC.sub.2 H.sub.5                                       121 3-C.sub.2 H.sub.5 CHC.sub.2 H.sub.5                                       122 4-t-C.sub.4 H.sub.9                                                                             CHC.sub.2 H.sub.5                                       123 4-Cyclohexyl      CHC.sub.2 H.sub.5                                       124 3-CH.sub.2 C.sub.6 H.sub.5                                                                      CHC.sub.2 H.sub.5                                       125 2-OCH.sub.3       CHC.sub.2 H.sub.5                                       126 3-OCH.sub.3       CHC.sub.2 H.sub.5                                       127 4-OCH.sub.3       CHC.sub.2 H.sub.5                                       128 2-O-i-C.sub.3 H.sub.7                                                                           CHC.sub.2 H.sub.5                                       129 3-OCH.sub.2 C.sub.6 H.sub.5                                                                     CHC.sub.2 H.sub.5                                       130 3-CF.sub.3        CHC.sub.2 H.sub.5                                       131 3-NO.sub.2        CHC.sub.2 H.sub.5                                       132 4-NO.sub.2        CHC.sub.2 H.sub.5                                       133 3-Cyano           CHC.sub.2 H.sub.5                                       134 2-Cl, 4-CH.sub.3  CHC.sub.2 H.sub.5                                       135 2-COOCH.sub.3     CHC.sub.2 H.sub.5                                       136 4-CH.sub.2 OCH.sub.3                                                                            CHC.sub.2 H.sub.5                                       137 4-COCH.sub.3      CHC.sub.2 H.sub.5                                       138 2-CH.sub.3 -4-COCH.sub.3                                                                        CHC.sub.2 H.sub.5                                       139 4-C(CH.sub.3)NOCH.sub.2 CHCH.sub.2                                                              CHC.sub.2 H.sub.5                                       140 2-CH.sub.3 -4-C(CH.sub.3)NOCH.sub.2 CHCH.sub.2                                                  CHC.sub.2 H.sub.5                                       __________________________________________________________________________

                                      TABLE III                                   __________________________________________________________________________     ##STR13##                                                                                                m.p.                                              No. Q.sub.m           X     (°C.)                                                                       δ (CC .sub.--H)                        __________________________________________________________________________    1   3-F               CHOCH.sub.3                                             2   2,6-F.sub.29      CHOCH.sub.3                                                                         114-116                                           3   2-Cl              CHOCH.sub.3                                             4   3-Cl              CHOCH.sub.3                                             5   4-Cl              CHOCH.sub.3                                             6   2,6-Cl.sub.2      CHOCH.sub.3                                             7   3,4-Cl.sub.2      CHOCH.sub.3                                             8   3-Br              CHOCH.sub.3                                             9   4-I               CHOCH.sub.3                                             10  2-Cl, 6-F         CHOCH.sub.3                                             11  2-CH.sub.3        CHOCH.sub.3                                                                         110-112                                           12  3-CH.sub.3        CHOCH.sub.3                                                                         oil  6.44/                                                                         6.73                                         13  4-CH.sub.3        CHOCH.sub.3                                             14  2,4-(CH.sub.3).sub.2                                                                            CHOCH.sub.3                                             15  2,4,6-(CH.sub.3).sub.3                                                                          CHOCH.sub.3                                             16  3-C.sub.2 H.sub.5 CHOCH.sub.3                                             17  4-t-C.sub.4 H.sub.9                                                                             CHOCH.sub.3                                             18  4-Cyclohexyl      CHOCH.sub.3                                             19  3-CH.sub.2 C.sub.6 H.sub.5                                                                      CHOCH.sub.3                                             20  2-OCH.sub.3       CHOCH.sub.3                                             21  3-OCH.sub.3       CHOCH.sub.3                                             22  4-OCH.sub.3       CHOCH.sub. 3                                            23  2-O-i-C.sub.3 H.sub.7                                                                           CHOCH.sub.3                                             24  3-OCH.sub.2 C.sub.6 H.sub.5                                                                     CHOCH.sub.3                                             25  3-CF.sub.3        CHOCH.sub.3                                             26  3-NO.sub.2        CHOCH.sub.3                                             27  2-Cyano           CHOCH.sub.3                                                                         141-142                                           28  3-Cyano           CHOCH.sub.3                                                                         93-94                                             29  2-Cl, 4-CH.sub.3  CHOCH.sub.3                                             30  2-COOCH.sub.3     CHOCH.sub.3                                             31  4-CH.sub.2 OCH.sub.3                                                                            CHOCH.sub.3                                             32  4-COCH.sub.3      CHOCH.sub.3                                             33  2-CH.sub.3 -4-COCH.sub.3                                                                        CHOCH.sub.3                                             34  4-C(CH.sub.3)NOCH.sub.2 CHCH.sub.2                                                              CHOCH.sub.3                                             35  2-CH.sub.3 -4-C(CH.sub.3)NOCH.sub.2 CHCH.sub.2                                                  CHOCH.sub.3                                             36  3-F               NOCH.sub.3                                              37  2,6-F.sub.2       NOCH.sub.3                                                                          108-110                                           38  2-Cl              NOCH.sub.3                                              39  3-Cl              NOCH.sub.3                                              40  4-Cl              NOCH.sub.3                                              41  2,6-Cl.sub.2      NOCH.sub.3                                              42  3,4-Cl.sub.2      NOCH.sub.3                                              43  3-Br              NOCH.sub.3                                              44  4-I               NOCH.sub.3                                              45  2-Cl, 6-F         NOCH.sub.3                                              46  2-CH.sub.3        NOCH.sub.3                                                                          91-94                                             47  3-CH.sub.3        NOCH.sub.3                                                                          oil  6.45/                                                                         7.51                                         48  4-CH.sub.3        NOCH.sub.3                                              49  2,4-(CH.sub.3).sub.2                                                                            NOCH.sub.3                                              50  2,4,6-(CH.sub.3).sub.3                                                                          NOCH.sub.3                                              51  3-C.sub.2 H.sub.5 NOCH.sub.3                                              52  4-t-C.sub.4 H.sub.9                                                                             NOCH.sub.3                                              53  4-Cyclohexyl      NOCH.sub.3                                              54  3-CH.sub.2 C.sub.6 H.sub.5                                                                      NOCH.sub.3                                              55  2-OCH.sub.3       NOCH.sub.3                                                                          87-88                                             56  3-OCH.sub.3       NOCH.sub.3                                              57  4-OCH.sub.3       NOCH.sub.3                                              58  2-O-i-C.sub.3 H.sub.7                                                                           NOCH.sub.3                                              59  3-OCH.sub.2 C.sub.6 H.sub.5                                                                     NOCH.sub.3                                              60  3-CF.sub.3        NOCH.sub.3                                              61  3-NO.sub.2        NOCH.sub.3                                              62  2-Cyano           NOCH.sub.3                                                                          127-129                                           63  3-Cyano           NOCH.sub.3                                                                          104-106                                           64  2-Cl, 4-CH.sub.3  NOCH.sub.3                                              65  2-COOCH.sub.3     NOCH.sub.3                                              66  4-CH.sub.2 OCH.sub.3                                                                            NOCH.sub.3                                              67  4-COCH.sub.3      NOCH.sub.3                                              68  2-CH.sub.3 -4-COCH.sub.3                                                                        NOCH.sub.3                                              69  4-C(CH.sub.3)NOCH.sub.2 CHCH.sub.2                                                              NOCH.sub.3                                              70  2-CH.sub.3 -4-C(CH.sub.3)NOCH.sub.2 CHCH.sub.2                                                  NOCH.sub.3                                              71  3-F               CHCH.sub.3                                              72  2,6-F.sub.2       CHCH.sub.3                                              73  2-Cl              CHCH.sub.3                                              74  3-Cl              CHCH.sub.3                                              75  4-Cl              CHCH.sub.3                                              76  2,6-Cl.sub.2      CHCH.sub.3                                              77  3,4-Cl.sub.2      CHCH.sub.3                                              78  3-Br              CHCH.sub.3                                              79  4-I               CHCH.sub.3                                              80  2-Cl, 6-F         CHCH.sub.3                                              81  2-CH.sub.3        CHCH.sub.3                                              82  3-CH.sub.3        CHCH.sub.3                                              83  4-CH.sub.3        CHCH.sub.3                                              84  2,4-(CH.sub.3).sub.2                                                                            CHCH.sub.3                                              85  2,4,6-(CH.sub.3).sub.3                                                                          CHCH.sub.3                                              86  3-C.sub.2 H.sub.5 CHCH.sub.3                                              87  4-t-C.sub.4 H.sub.9                                                                             CHCH.sub.3                                              88  4-Cyclohexyl      CHCH.sub.3                                              89  3-CH.sub.2 C.sub.6 H.sub.5                                                                      CHCH.sub.3                                              90  2-OCH.sub.3       CHCH.sub.3                                              91  3-OCH.sub.3       CHCH.sub.3                                              92  4-OCH.sub.3       CHCH.sub.3                                              93  2-O-i-C.sub.3 H.sub.7                                                                           CHCH.sub.3                                              94  3-OCH.sub.2 C.sub.6 H.sub.5                                                                     CHCH.sub.3                                              95  3-CF.sub.3        CHCH.sub.3                                              96  3-NO.sub.2        CHCH.sub.3                                              97  2-Cyano           CHCH.sub.3                                              98  3-Cyano           CHCH.sub.3                                              99  2-Cl, 4-CH.sub.3  CHCH.sub.3                                              100 2-COOCH.sub.3     CHCH.sub.3                                              101 4-CH.sub.2 OCH.sub.3                                                                            CHCH.sub.3                                              102 4-COCH.sub.3      CHCH.sub.3                                              103 2-CH.sub.3 -4-COCH.sub.3                                                                        CHCH.sub.3                                              104 4-C(CH.sub.3)NOCH.sub.2 CHCH.sub.2                                                              CHCH.sub.3                                              105 2-CH.sub.3 -4-C(CH.sub.3)NOCH.sub.2 CHCH.sub.2                                                  CHCH.sub.3                                              106 3-F               CHC.sub.2 H.sub.5                                       107 2,6-F.sub.2       CHC.sub.2 H.sub.5                                       108 2-Cl              CHC.sub.2 H.sub.5                                       109 3-Cl              CHC.sub.2 H.sub.5                                       110 4-Cl              CHC.sub.2 H.sub.5                                       111 2,6-Cl.sub.2      CHC.sub.2 H.sub.5                                       112 3,4-Cl.sub.2      CHC.sub.2 H.sub.5                                       113 3-Br              CHC.sub.2 H.sub.5                                       114 4-I               CHC.sub.2 H.sub.5                                       115 2-Cl, 6-F         CHC.sub.2 H.sub.5                                       116 2-CH.sub.3        CHC.sub.2 H.sub.5                                       117 3-CH.sub.3        CHC.sub.2 H.sub.5                                       118 4-CH.sub.3        CHC.sub.2 H.sub. 5                                      119 2,4-(CH.sub.3).sub.2                                                                            CHC.sub.2 H.sub.5                                       120 2,4,6-(CH.sub.3).sub.3                                                                          CHC.sub.2 H.sub.5                                       121 3-C.sub.2 H.sub.5 CHC.sub.2 H.sub.5                                       122 4-t-C.sub.4 H.sub.9                                                                             CHC.sub.2 H.sub.5                                       123 4-Cyclohexyl      CHC.sub.2 H.sub.5                                       124 3-CH.sub.2 C.sub.6 H.sub.5                                                                      CHC.sub.2 H.sub.5                                       125 2-OCH.sub.3       CHC.sub.2 H.sub.5                                       126 3-OCH.sub.3       CHC.sub.2 H.sub.5                                       127 4-OCH.sub.3       CHC.sub.2 H.sub.5                                       128 2-O-i-C.sub.3 H.sub.7                                                                           CHC.sub.2 H.sub.5                                       129 3-OCH.sub.2 C.sub.6 H.sub.5                                                                     CHC.sub.2 H.sub.5                                       130 3-CF.sub.3        CHC.sub.2 H.sub.5                                       131 3-NO.sub.2        CHC.sub.2 H.sub.5                                       132 2-Cyano           CHC.sub.2 H.sub.5                                       133 3-Cyano           CHC.sub.2 H.sub.5                                       134 2-Cl, 4-CH.sub.3  CHC.sub.2 H.sub.5                                       135 2-COOCH.sub.3     CHC.sub.2 H.sub.5                                       136 4-CH.sub.2 OCH.sub.3                                                                            CHC.sub.2 H.sub.5                                       137 4-COCH.sub.3      CHC.sub.2 H.sub.5                                       138 2-CH.sub.3 -4-COCH.sub.3                                                                        CHC.sub.2 H.sub.5                                       139 4-C(CH.sub.3)NOCH.sub.2 CHCH.sub.2                                                              CHC.sub.2 H.sub.5                                       140 2-CH.sub.3 -4-C(CH.sub.3)NOCH.sub.2 CHCH.sub.2                                                  CHC.sub.2 H.sub.5                                       __________________________________________________________________________

                                      TABLE IV                                    __________________________________________________________________________     ##STR14##                                                                                                  m.p.                                            No.                                                                              Q.sub.m           R  X     (°C.)                                                                       δ (CC .sub.-- H)                     __________________________________________________________________________     1 3-F               H  CHOCH.sub.3                                                                         165-168                                          2 2,6-F.sub.2       H  CHOCH.sub.3                                            3 2-Cl              H  CHOCH.sub.3                                            4 3-Cl              H  CHOCH.sub.3                                            5 4-Cl              H  CHOCH.sub.3                                            6 2,6-Cl.sub.2      H  CHOCH.sub.3                                            7 3,4-Cl.sub.2      H  CHOCH.sub.3                                            8 3-Br              H  CHOCH.sub.3                                            9 4-I               H  CHOCH.sub.3                                            10                                                                              2-Cl, 6-F         H  CHOCH.sub.3                                            11                                                                              2-CH.sub.3        H  CHOCH.sub.3                                            12                                                                              3-CH.sub.3        H  CHOCH.sub.3                                                                         150-152                                          13                                                                              4-CH.sub.3        H  CHOCH.sub.3                                            14                                                                              2,4-(CH.sub.3).sub.2                                                                            H  CHOCH.sub.3                                            15                                                                              2,4,6-(CH.sub.3).sub.3                                                                          H  CHOCH.sub.3                                            16                                                                              3-C.sub.2 H.sub.5 H  CHOCH.sub.3                                            17                                                                              4-t-C.sub.4 H.sub.9                                                                             H  CHOCH.sub.3                                            18                                                                              4-Cyclohexyl      H  CHOCH.sub.3                                            19                                                                              3-CH.sub.2 C.sub.6 H.sub.5                                                                      H  CHOCH.sub.3                                            20                                                                              2-OCH.sub.3       H  CHOCH.sub.3                                            21                                                                              3-OCH.sub.3       H  CHOCH.sub.3                                            22                                                                              4-OCH.sub.3       H  CHOCH.sub.3                                            23                                                                              2-O-i-C.sub.3 H.sub.7                                                                           H  CHOCH.sub.3                                            24                                                                              3-OCH.sub.2 C.sub.6 H.sub.5                                                                     H  CHOCH.sub.3                                            25                                                                              3-CF.sub.3        H  CHOCH.sub.3                                            26                                                                              3-NO.sub.2        H  CHOCH.sub.3                                            27                                                                              4-NO.sub.2        H  CHOCH.sub.3                                            28                                                                              3-Cyano           H  CHOCH.sub.3                                            29                                                                              2-Cl, 4-CH.sub.3  H  CHOCH.sub.3                                            30                                                                              2-COOCH.sub.3     H  CHOCH.sub.3                                                                         140-143                                          31                                                                              4-CH.sub.2 OCH.sub.3                                                                            H  CHOCH.sub.3                                            32                                                                              4-COCH.sub.3      H  CHOCH.sub.3                                            33                                                                              2-CH.sub.3 -4-COCH.sub.3                                                                        H  CHOCH.sub.3                                            34                                                                              4-C(CH.sub.3)NOCH.sub.2 CHCH.sub.2                                                              H  CHOCH.sub.3                                            35                                                                              2-CH.sub.3 -4-C(CH.sub.3)NOCH.sub.2 CHCH.sub.2                                                  H  CHOCH.sub.3                                            36                                                                              3-F               CH.sub.3                                                                         CHOCH.sub.3                                            37                                                                              2,6-F.sub.2       CH.sub.3                                                                         CHOCH.sub.3                                            38                                                                              2-Cl              CH.sub.3                                                                         CHOCH.sub.3                                            39                                                                              3-Cl              CH.sub.3                                                                         CHOCH.sub.3                                            40                                                                              4-Cl              CH.sub.3                                                                         CHOCH.sub.3                                            41                                                                              2,6-Cl.sub.2      CH.sub.3                                                                         CHOCH.sub.3                                            42                                                                              3,4-Cl.sub.2      CH.sub.3                                                                         CHOCH.sub.3                                            43                                                                              3-Br              CH.sub.3                                                                         CHOCH.sub.3                                            44                                                                              4-I               CH.sub.3                                                                         CHOCH.sub.3                                            45                                                                              2-Cl, 6-F         CH.sub.3                                                                         CHOCH.sub.3                                            46                                                                              2-CH.sub.3        CH.sub.3                                                                         CHOCH.sub.3                                            47                                                                              3-CH.sub.3        CH.sub.3                                                                         CHOCH.sub.3                                            48                                                                              4-CH.sub.3        CH.sub.3                                                                         CHOCH.sub.3                                            49                                                                              2,4-(CH.sub.3).sub.2                                                                            CH.sub.3                                                                         CHOCH.sub.3                                            50                                                                              2,4,6-(CH.sub.3).sub.3                                                                          CH.sub.3                                                                         CHOCH.sub.3                                            51                                                                              3-C.sub.2 H.sub.5 CH.sub.3                                                                         CHOCH.sub.3                                            52                                                                              4-t-C.sub.4 H.sub.9                                                                             CH.sub.3                                                                         CHOCH.sub.3                                            53                                                                              4-Cyclohexyl      CH.sub.3                                                                         CHOCH.sub.3                                            54                                                                              3-CH.sub.2 C.sub.6 H.sub.5                                                                      CH.sub.3                                                                         CHOCH.sub.3                                            55                                                                              2-OCH.sub.3       CH.sub.3                                                                         CHOCH.sub.3                                            56                                                                              3-OCH.sub.3       CH.sub.3                                                                         CHOCH.sub.3                                            57                                                                              4-OCH.sub.3       CH.sub.3                                                                         CHOCH.sub.3                                            58                                                                              2-O-i-C.sub.3 H.sub.7                                                                           CH.sub.3                                                                         CHOCH.sub.3                                            59                                                                              3-OCH.sub.2 C.sub.6 H.sub.5                                                                     CH.sub.3                                                                         CHOCH.sub.3                                            60                                                                              3-CF.sub.3        CH.sub.3                                                                         CHOCH.sub.3                                            61                                                                              3-NO.sub.2        CH.sub.3                                                                         CHOCH.sub.3                                            62                                                                              4-NO.sub.2        CH.sub.3                                                                         CHOCH.sub.3                                            63                                                                              3-Cyano           CH.sub.3                                                                         CHOCH.sub.3                                            64                                                                              2-Cl, 4-CH.sub.3  CH.sub.3                                                                         CHOCH.sub.3                                            65                                                                              2-COOCH.sub.3     CH.sub.3                                                                         CHOCH.sub.3                                            66                                                                              4-CH.sub.2 OCH.sub.3                                                                            CH.sub.3                                                                         CHOCH.sub.3                                            67                                                                              4-COCH.sub.3      CH.sub.3                                                                         CHOCH.sub.3                                            68                                                                              2-CH.sub.3 -4-COCH.sub.3                                                                        CH.sub.3                                                                         CHOCH.sub.3                                            69                                                                              4-C(CH.sub.3)NOCH.sub.2 CHCH.sub.2                                                              CH.sub.3                                                                         CHOCH.sub.3                                            70                                                                              2-CH.sub.3 -4-C(CH.sub.3)NOCH.sub.2 CHCH.sub.2                                                  CH.sub.3                                                                         CHOCH.sub.3                                            71                                                                              3-F               H  NOCH.sub.3                                                                          138-141                                          72                                                                              2,6-F.sub.2       H  NOCH.sub.3                                             73                                                                              2-Cl              H  NOCH.sub.3                                             74                                                                              3-Cl              H  NOCH.sub.3                                             75                                                                              4-Cl              H  NOCH.sub.3                                             76                                                                              2,6-Cl.sub.2      H  NOCH.sub.3                                             77                                                                              3,4-Cl.sub.2      H  NOCH.sub.3                                             78                                                                              3-Br              H  NOCH.sub.3                                             79                                                                              4-I               H  NOCH.sub.3                                             80                                                                              2-Cl, 6-F         H  NOCH.sub.3                                             81                                                                              2-CH.sub.3        H  NOCH.sub.3                                             82                                                                              3-CH.sub.3        H  NOCH.sub.3                                                                          125-127                                          83                                                                              4-CH.sub.3        H  NOCH.sub.3                                             84                                                                              2,4-(CH.sub.3).sub.2                                                                            H  NOCH.sub.3                                             85                                                                              2,4,6-(CH.sub.3).sub.3                                                                          H  NOCH.sub.3                                             86                                                                              3-C.sub.2 H.sub.5 H  NOCH.sub.3                                             87                                                                              4-t-C.sub.4 H.sub.9                                                                             H  NOCH.sub.3                                             88                                                                              4-Cyclohexyl      H  NOCH.sub.3                                              89                                                                             3-CH.sub.2 C.sub.6 H.sub.5                                                                      H  NOCH.sub.3                                             90                                                                              2-OCH.sub.3       H  NOCH.sub.3                                             91                                                                              3-OCH.sub.3       H  NOCH.sub.3                                             92                                                                              4-OCH.sub.3       H  NOCH.sub.3                                             93                                                                              2-O-i-C.sub.3 H.sub.7                                                                           H  NOCH.sub.3                                             94                                                                              3-OCH.sub.2 C.sub.6 H.sub.5                                                                     H  NOCH.sub.3                                             95                                                                              3-CF.sub.3        H  NOCH.sub.3                                             96                                                                              3-NO.sub.2        H  NOCH.sub.3                                             97                                                                              4-NO.sub.2        H  NOCH.sub.3                                             98                                                                              3-Cyano           H  NOCH.sub.3                                             99                                                                              2-Cl, 4-CH.sub.3  H  NOCH.sub.3                                            100                                                                              2-COOCH.sub.3     H  NOCH.sub.3                                                                          165                                                                           (de-                                                                          comp.)                                          101                                                                              4-CH.sub.2 OCH.sub.3                                                                            H  NOCH.sub.3                                            102                                                                              4-COCH.sub.3      H  NOCH.sub.3                                            103                                                                              2-CH.sub.3 -4-COCH.sub.3                                                                        H  NOCH.sub.3                                            104                                                                              4-C(CH.sub.3)NOCH.sub.2 CHCH.sub.2                                                              H  NOCH.sub.3                                            105                                                                              2-CH.sub.3 -4-C(CH.sub.3)NOCH.sub.2 CHCH.sub.2                                                  H  NOCH.sub.3                                            106                                                                              3-F               CH.sub.3                                                                         NOCH.sub.3                                            107                                                                              2,6-F.sub.2       CH.sub.3                                                                         NOCH.sub.3                                            108                                                                              2-Cl              CH.sub.3                                                                         NOCH.sub.3                                            109                                                                              3-Cl              CH.sub.3                                                                         NOCH.sub.3                                            110                                                                              4-Cl              CH.sub.3                                                                         NOCH.sub.3                                            111                                                                              2,6-Cl.sub.2      CH.sub.3                                                                         NOCH.sub.3                                            112                                                                              3,4-Cl.sub.2      CH.sub.3                                                                         NOCH.sub.3                                            113                                                                              3-Br              CH.sub.3                                                                         NOCH.sub.3                                            114                                                                              4-I               CH.sub.3                                                                         NOCH.sub.3                                            115                                                                              2-Cl, 6-F         CH.sub.3                                                                         NOCH.sub.3                                            116                                                                              2-CH.sub.3        CH.sub.3                                                                         NOCH.sub.3                                            117                                                                              3-CH.sub.3        CH.sub.3                                                                         NOCH.sub.3                                            118                                                                              4-CH.sub.3        CH.sub.3                                                                         NOCH.sub.3                                            119                                                                              2,4-(CH.sub.3).sub.2                                                                            CH.sub.3                                                                         NOCH.sub.3                                            120                                                                              2,4,6-(CH.sub.3).sub.3                                                                          CH.sub.3                                                                         NOCH.sub.3                                            121                                                                              3-C.sub.2 H.sub.5 CH.sub.3                                                                         NOCH.sub.3                                            122                                                                              4-t-C.sub.4 H.sub.9                                                                             CH.sub.3                                                                         NOCH.sub.3                                            123                                                                              4-Cyclohexyl      CH.sub.3                                                                         NOCH.sub.3                                            124                                                                              3-CH.sub.2 C.sub.6 H.sub.5                                                                      CH.sub.3                                                                         NOCH.sub.3                                            125                                                                              2-OCH.sub.3       CH.sub.3                                                                         NOCH.sub.3                                            126                                                                              3-OCH.sub.3       CH.sub.3                                                                         NOCH.sub.3                                            127                                                                              4-OCH.sub.3       CH.sub.3                                                                         NOCH.sub.3                                            128                                                                              2-O-i-C.sub.3 H.sub.7                                                                           CH.sub.3                                                                         NOCH.sub.3                                            129                                                                              3-OCH.sub.2 C.sub.6 H.sub.5                                                                     CH.sub.3                                                                         NOCH.sub.3                                            130                                                                              3-CF.sub.3        CH.sub.3                                                                         NOCH.sub.3                                            131                                                                              3-NO.sub.2        CH.sub.3                                                                         NOCH.sub.3                                            132                                                                              4-NO.sub.2        CH.sub.3                                                                         NOCH.sub.3                                            133                                                                              3-Cyano           CH.sub.3                                                                         NOCH.sub.3                                            134                                                                              2-Cl, 4-CH.sub.3  CH.sub.3                                                                         NOCH.sub.3                                            135                                                                              2-COOCH.sub.3     CH.sub.3                                                                         NOCH.sub.3                                            136                                                                              4-CH.sub.2 OCH.sub.3                                                                            CH.sub.3                                                                         NOCH.sub.3                                            137                                                                              4-COCH.sub.3      CH.sub.3                                                                         NOCH.sub.3                                            138                                                                              2-CH.sub.3 -4-COCH.sub.3                                                                        CH.sub.3                                                                         NOCH.sub.3                                            139                                                                              4-C(CH.sub.3)NOCH.sub.2 CHCH.sub.2                                                              CH.sub.3                                                                         NOCH.sub. 3                                           140                                                                              2-CH.sub.3 -4-C(CH.sub.3)NOCH.sub.2 CHCH.sub.2                                                  CH.sub.3                                                                         NOCH.sub.3                                            141                                                                              3-F               H  CHCH.sub.3                                            142                                                                              2,6-F.sub.2       H  CHCH.sub.3                                            143                                                                              2-Cl              H  CHCH.sub.3                                            144                                                                              3-Cl              H  CHCH.sub.3                                            145                                                                              4-Cl              H  CHCH.sub.3                                            146                                                                              2,6-Cl.sub.2      H  CHCH.sub.3                                            147                                                                              3,4-Cl.sub.2      H  CHCH.sub.3                                            148                                                                              3-Br              H  CHCH.sub.3                                            149                                                                              4-I               H  CHCH.sub.3                                            150                                                                              2-Cl, 6-F         H  CHCH.sub.3                                            151                                                                              2-CH.sub.3        H  CHCH.sub.3                                            152                                                                              3-CH.sub.3        H  CHCH.sub.3                                            153                                                                              4-CH.sub.3        H  CHCH.sub.3                                            154                                                                              2,4-(CH.sub.3).sub.2                                                                            H  CHCH.sub.3                                            155                                                                              2,4,6-(CH.sub.3).sub.3                                                                          H  CHCH.sub.3                                            156                                                                              3-C.sub.2 H.sub.5 H  CHCH.sub.3                                            157                                                                              4-t-C.sub.4 H.sub.9                                                                             H  CHCH.sub.3                                            158                                                                              4-Cyclohexyl      H  CHCH.sub.3                                            159                                                                              3-CH.sub.2 C.sub.6 H.sub.5                                                                      H  CHCH.sub.3                                            160                                                                              2-OCH.sub.3       H  CHCH.sub.3                                            161                                                                              3-OCH.sub.3       H  CHCH.sub.3                                            162                                                                              4-OCH.sub.3       H  CHCH.sub.3                                            163                                                                              2-O-i-C.sub.3 H.sub.7                                                                           H  CHCH.sub.3                                            164                                                                              3-OCH.sub.2 C.sub.6 H.sub.5                                                                     H  CHCH.sub.3                                            165                                                                              3-CF.sub.3        H  CHCH.sub.3                                            166                                                                              3-NO.sub.2        H  CHCH.sub.3                                            167                                                                              4-NO.sub.2        H  CHCH.sub.3                                            168                                                                              3-Cyano           H  CHCH.sub.3                                            169                                                                              2-Cl, 4-CH.sub.3  H  CHCH.sub. 3                                           170                                                                              2-COOCH.sub.3     H  CHCH.sub.3                                            171                                                                              4-CH.sub.2 OCH.sub.3                                                                            H  CHCH.sub.3                                            172                                                                              4-COCH.sub.3      H  CHCH.sub.3                                            173                                                                              2-CH.sub.3 -4-COCH.sub.3                                                                        H  CHCH.sub.3                                            174                                                                              4-C(CH.sub.3)NOCH.sub.2 CHCH.sub.2                                                              H  CHCH.sub.3                                            175                                                                              2-CH.sub.3 -4-C(CH.sub.3)NOCH.sub.2 CHCH.sub.2                                                  H  CHCH.sub.3                                            176                                                                              3-F               CH.sub.3                                                                         CHCH.sub.3                                            177                                                                              2,6-F.sub.2       CH.sub.3                                                                         CHCH.sub.3                                            178                                                                              2-Cl              CH.sub.3                                                                         CHCH.sub.3                                            179                                                                              3-Cl              CH.sub.3                                                                         CHCH.sub.3                                            180                                                                              4-Cl              CH.sub.3                                                                         CHCH.sub.3                                            181                                                                              2,6-Cl.sub.2      CH.sub.3                                                                         CHCH.sub.3                                            182                                                                              3,4-Cl.sub.2      CH.sub.3                                                                         CHCH.sub.3                                            183                                                                              3-Br              CH.sub.3                                                                         CHCH.sub.3                                            184                                                                              4-I               CH.sub.3                                                                         CHCH.sub.3                                            185                                                                              2-Cl, 6-F         CH.sub.3                                                                         CHCH.sub.3                                            186                                                                              2-CH.sub.3        CH.sub.3                                                                         CHCH.sub.3                                            187                                                                              3-CH.sub.3        CH.sub.3                                                                         CHCH.sub.3                                            188                                                                              4-CH.sub.3        CH.sub.3                                                                         CHCH.sub.3                                            189                                                                              2,4-(CH.sub.3).sub.2                                                                            CH.sub.3                                                                         CHCH.sub.3                                            190                                                                              2,4,6-(CH.sub.3).sub.3                                                                          CH.sub.3                                                                         CHCH.sub.3                                            191                                                                              3-C.sub.2 H.sub.5 CH.sub.3                                                                         CHCH.sub.3                                            192                                                                              4-t-C.sub.4 H.sub.9                                                                             CH.sub.3                                                                         CHCH.sub.3                                            193                                                                              4-Cyclohexyl      CH.sub.3                                                                         CHCH.sub.3                                            194                                                                              3-CH.sub.2 C.sub.6 H.sub.5                                                                      CH.sub.3                                                                         CHCH.sub.3                                            195                                                                              2-OCH.sub.3       CH.sub.3                                                                         CHCH.sub.3                                            196                                                                              3-OCH.sub.3       CH.sub.3                                                                         CHCH.sub.3                                            197                                                                              4-OCH.sub.3       CH.sub.3                                                                         CHCH.sub.3                                            198                                                                              2-O-i-C.sub.3 H.sub.7                                                                           CH.sub.3                                                                         CHCH.sub.3                                            199                                                                              3-OCH.sub.2 C.sub.6 H.sub.5                                                                     CH.sub.3                                                                         CHCH.sub.3                                            200                                                                              3-CF.sub.3        CH.sub.3                                                                         CHCH.sub.3                                            201                                                                              3-NO.sub.2        CH.sub.3                                                                         CHCH.sub.3                                            202                                                                              4-NO.sub.2        CH.sub.3                                                                         CHCH.sub.3                                            203                                                                              3-Cyano           CH.sub.3                                                                         CHCH.sub.3                                            204                                                                              2-Cl, 4-CH.sub.3  CH.sub.3                                                                         CHCH.sub.3                                            205                                                                              2-COOCH.sub.3     CH.sub.3                                                                         CHCH.sub.3                                            206                                                                              4-CH.sub.2 OCH.sub.3                                                                            CH.sub.3                                                                         CHCH.sub.3                                            207                                                                              4-COCH.sub.3      CH.sub.3                                                                         CHCH.sub.3                                            208                                                                              2-CH.sub.3 -4-COCH.sub.3                                                                        CH.sub.3                                                                         CHCH.sub.3                                            209                                                                              4-C(CH.sub.3)NOCH.sub.2 CHCH.sub.2                                                              CH.sub.3                                                                         CHCH.sub.3                                            210                                                                              2-CH.sub.3 -4-C(CH.sub.3)NOCH.sub.2 CHCH.sub.2                                                  CH.sub.3                                                                         CHCH.sub.3                                            211                                                                              3-F               H  CHC.sub.2 H.sub.5                                     212                                                                              2,6-F.sub.2       H  CHC.sub.2 H.sub.5                                     213                                                                              2-Cl              H  CHC.sub.2 H.sub.5                                     214                                                                              3-Cl              H  CHC.sub.2 H.sub.5                                     215                                                                              4-Cl              H  CHC.sub.2 H.sub.5                                     216                                                                              2,6-Cl.sub.2      H  CHC.sub.2 H.sub.5                                     217                                                                              3,4-Cl.sub.2      H  CHC.sub.2 H.sub.5                                     218                                                                              3-Br              H  CHC.sub.2 H.sub.5                                     219                                                                              4-I               H  CHC.sub.2 H.sub.5                                     220                                                                              2-Cl, 6-F         H  CHC.sub.2 H.sub. 5                                    221                                                                              2-CH.sub.3        H  CHC.sub.2 H.sub.5                                     222                                                                              3-CH.sub.3        H  CHC.sub.2 H.sub.5                                     223                                                                              4-CH.sub.3        H  CHC.sub.2 H.sub.5                                     224                                                                              2,4-(CH.sub.3).sub.2                                                                            H  CHC.sub.2 H.sub.5                                     225                                                                              2,4,6-(CH.sub.3).sub.3                                                                          H  CHC.sub.2 H.sub.5                                     226                                                                              3-C.sub.2 H.sub.5 H  CHC.sub.2 H.sub.5                                     227                                                                              4-t-C.sub.4 H.sub.9                                                                             H  CHC.sub.2 H.sub.5                                     228                                                                              4-Cyclohexyl      H  CHC.sub.2 H.sub.5                                     229                                                                              3-CH.sub.2 C.sub.6 H.sub.5                                                                      H  CHC.sub.2 H.sub.5                                     230                                                                              2-OCH.sub.3       H  CHC.sub.2 H.sub.5                                     231                                                                              3-OCH.sub.3       H  CHC.sub.2 H.sub.5                                     232                                                                              4-OCH.sub.3       H  CHC.sub.2 H.sub.5                                     233                                                                              2-O-i-C.sub.3 H.sub.7                                                                           H  CHC.sub.2 H.sub.5                                     234                                                                              3-OCH.sub.2 C.sub.6 H.sub.5                                                                     H  CHC.sub.2 H.sub.5                                     235                                                                              3-CF.sub.3        H  CHC.sub.2 H.sub.5                                     236                                                                              3-NO.sub.2        H  CHC.sub.2 H.sub.5                                     237                                                                              4-NO.sub.2        H  CHC.sub.2 H.sub.5                                     238                                                                              3-Cyano           H  CHC.sub.2 H.sub.5                                     239                                                                              2-Cl, 4-CH.sub.3  H  CHC.sub.2 H.sub.5                                     240                                                                              2-COOCH.sub.3     H  CHC.sub.2 H.sub.5                                     241                                                                              4-CH.sub.2 OCH.sub.3                                                                            H  CHC.sub.2 H.sub.5                                     242                                                                              4-COCH.sub.3      H  CHC.sub.2 H.sub.5                                     243                                                                              2-CH.sub.3 -4-COCH.sub. 3                                                                       H  CHC.sub.2 H.sub.5                                     244                                                                              4-C(CH.sub.3)NOCH.sub.2 CHCH.sub.2                                                              H  CHC.sub.2 H.sub.5                                     245                                                                              2-CH.sub.3 -4-C(CH.sub.3)NOCH.sub.2 CHCH.sub.2                                                  H  CHC.sub.2 H.sub.5                                     246                                                                              3-F               CH.sub.3                                                                         CHC.sub.2 H.sub.5                                     247                                                                              2,6-F.sub.2       CH.sub.3                                                                         CHC.sub.2 H.sub.5                                     248                                                                              2-Cl              CH.sub.3                                                                         CHC.sub.2 H.sub.5                                     249                                                                              3-Cl              CH.sub.3                                                                         CHC.sub.2 H.sub.5                                     250                                                                              4-Cl              CH.sub.3                                                                         CHC.sub.2 H.sub.5                                     251                                                                              2,6-Cl.sub.2      CH.sub.3                                                                         CHC.sub.2 H.sub.5                                     252                                                                              3,4-Cl.sub.2      CH.sub.3                                                                         CHC.sub.2 H.sub.5                                     253                                                                              3-Br              CH.sub.3                                                                         CHC.sub.2 H.sub.5                                     254                                                                              4-I               CH.sub.3                                                                         CHC.sub.2 H.sub.5                                     255                                                                              2-Cl, 6-F         CH.sub.3                                                                         CHC.sub.2 H.sub.5                                     256                                                                              2-CH.sub.3        CH.sub.3                                                                         CHC.sub.2 H.sub.5                                     257                                                                              3-CH.sub.3        CH.sub.3                                                                         CHC.sub.2 H.sub.5                                     258                                                                              4-CH.sub.3        CH.sub.3                                                                         CHC.sub.2 H.sub.5                                     259                                                                              2,4-(CH.sub.3).sub.2                                                                            CH.sub.3                                                                         CHC.sub.2 H.sub.5                                     260                                                                              2,4,6-(CH.sub.3).sub.3                                                                          CH.sub.3                                                                         CHC.sub.2 H.sub.5                                     261                                                                              3-C.sub.2 H.sub.5 CH.sub.3                                                                         CHC.sub.2 H.sub.5                                     262                                                                              4-t-C.sub.4 H.sub.9                                                                             CH.sub.3                                                                         CHC.sub.2 H.sub.5                                     263                                                                              4-Cyclohexyl      CH.sub.3                                                                         CHC.sub.2 H.sub.5                                     264                                                                              2-CH.sub.2 C.sub.6 H.sub.5                                                                      CH.sub.3                                                                         CHC.sub.2 H.sub.5                                     265                                                                              2-OCH.sub.3       CH.sub.3                                                                         CHC.sub.2 H.sub.5                                     266                                                                              3-OCH.sub.3       CH.sub.3                                                                         CHC.sub.2 H.sub.5                                     267                                                                              4-OCH.sub.3       CH.sub.3                                                                         CHC.sub.2 H.sub.5                                     268                                                                              2-O-i-C.sub.3 H.sub.7                                                                           CH.sub.3                                                                         CHC.sub.2 H.sub.5                                     269                                                                              3-OCH.sub.2 C.sub.6 H.sub.5                                                                     CH.sub.3                                                                         CHC.sub.2 H.sub.5                                     270                                                                              3-CF.sub.3        CH.sub.3                                                                         CHC.sub.2 H.sub.5                                     271                                                                              3-NO.sub.2        CH.sub.3                                                                         CHC.sub.2 H.sub.5                                     272                                                                              4-NO.sub.2        CH.sub.3                                                                         CHC.sub.2 H.sub.5                                     273                                                                              3-Cyano           CH.sub.3                                                                         CHC.sub.2 H.sub.5                                     274                                                                              2-Cl, 4-CH.sub.3  CH.sub.3                                                                         CHC.sub.2 H.sub.5                                     275                                                                              2-COOCH.sub.3     CH.sub.3                                                                         CHC.sub.2 H.sub.5                                     276                                                                              4-CH.sub.2 OCH.sub.3                                                                            CH.sub.3                                                                         CHC.sub.2 H.sub.5                                     277                                                                              4-COCH.sub.3      CH.sub.3                                                                         CHC.sub.2 H.sub.5                                     278                                                                              2-CH.sub.3 -4-COCH.sub.3                                                                        CH.sub.3                                                                         CHC.sub.2 H.sub.5                                     279                                                                              4-C(CH.sub.3)NOCH.sub.2 CHCH.sub.2                                                              CH.sub.3                                                                         CHC.sub.2 H.sub.5                                     280                                                                              2-CH.sub.3 -4-C(CH.sub.3)NOCH.sub.2 CHCH.sub.2                                                  CH.sub.3                                                                         CHC.sub.2 H.sub.5                                     __________________________________________________________________________

                  TABLE V                                                         ______________________________________                                         ##STR15##                                                                                                    Iso- m.p. δ                             No.  R           A      X       mer  (°C.)                                                                       (CC .sub.--H)                       ______________________________________                                        1    CH.sub.3    H      CHOCH.sub.3                                           2    t-C.sub.4 H.sub.9                                                                         H      CHOCH.sub.3                                           3    C.sub.6 H.sub.5                                                                           H      CHOCH.sub.3                                           4    2-ClC.sub.6 H.sub.4                                                                       H      CHOCH.sub.3                                           5    3-ClC.sub.6 H.sub.4                                                                       H      CHOCH.sub.3                                           6    4-ClC.sub.6 H.sub.4                                                                       H      CHOCH.sub.3                                           7    2-CH.sub.3 C.sub.6 H.sub.4                                                                H      CHOCH.sub.3                                           8    3-CH.sub.3 OC.sub.6 H.sub.4                                                               H      CHOCH.sub.3                                           9    4-Cyano-C.sub.6 H.sub.4                                                                   H      CHOCH.sub.3                                           10   2,6-F.sub.2C.sub.6 H.sub.3                                                                H      CHOCH.sub.3                                           11   3-Pyridyl   H      CHOCH.sub.3                                           12   2-Furyl     H      CHOCH.sub.3                                           13   β-Naphthyl                                                                           H      CHOCH.sub.3                                           14   CH.sub.3    CH.sub.3                                                                             CHOCH.sub.3                                           15   t-C.sub.4 H.sub.9                                                                         CH.sub.3                                                                             CHOCH.sub.3                                           16   C.sub.6 H.sub.5                                                                           CH.sub.3                                                                             CHOCH.sub.3                                           17   2-ClC.sub.6 H.sub.4                                                                       CH.sub.3                                                                             CHOCH.sub.3                                           18   3-ClC.sub.6 H.sub.4                                                                       CH.sub.3                                                                             CHOCH.sub.3                                           19   4-ClC.sub.6 H.sub.4                                                                       CH.sub.3                                                                             CHOCH.sub.3                                           20   2-CH.sub.3 C.sub.6 H.sub.4                                                                CH.sub.3                                                                             CHOCH.sub.3                                           21   3-CH.sub.3 OC.sub.6 H.sub.4                                                               CH.sub.3                                                                             CHOCH.sub.3                                           22   4-Cyano-C.sub.6 H.sub.4                                                                   CH.sub.3                                                                             CHOCH.sub.3                                           23   2,6-F.sub.2C.sub.6 H.sub.3                                                                CH.sub.3                                                                             CHOCH.sub.3                                           24   3-Pyridyl   CH.sub.3                                                                             CHOCH.sub.3                                           25   2-Furyl     CH.sub.3                                                                             CHOCH.sub.3                                           26   β-Napththyl                                                                          CH.sub.3                                                                             CHOCH.sub.3                                           27   CH.sub.3    C.sub.6 H.sub.5                                                                      CHOCH.sub.3                                           28   C.sub.6 H.sub.5                                                                           C.sub.6 H.sub.5                                                                      CHOCH.sub.3                                           29   2-CH.sub.3 C.sub.6 H.sub.4                                                                C.sub.6 H.sub.5                                                                      CHOCH.sub.3                                           30   2,6-F.sub.2 C.sub.6 H.sub.3                                                               C.sub.6 H.sub.5                                                                      CHOCH.sub.3                                           31   CH.sub.3    H      NOCH.sub.3                                            32   t-C.sub.4 H.sub.9                                                                         H      NOCH.sub.3                                            33   C.sub.6 H.sub.5                                                                           H      NOCH.sub.3                                            34   2-ClC.sub.6 H.sub.4                                                                       H      NOCH.sub.3                                            35   3-ClC.sub.6 H.sub.4                                                                       H      NOCH.sub.3                                            36   4-ClC.sub.6 H.sub.4                                                                       H      NOCH.sub.3                                            37   2-CH.sub.3 C.sub.6 H.sub.4                                                                H      NOCH.sub.3                                            38   3-CH.sub.3 OC.sub.6 H.sub. 4                                                              H      NOCH.sub.3                                            39   4-Cyano-C.sub.6 H.sub.4                                                                   H      NOCH.sub.3                                            40   2,6-F.sub.2C.sub.6 H.sub.3                                                                H      NOCH.sub.3                                            41   3-Pyridyl   H      NOCH.sub.3                                            42   2-Furyl     H      NOCH.sub.3                                            43   β-Naphthyl                                                                           H      NOCH.sub.3                                            44   CH.sub.3    CH.sub.3                                                                             NOCH.sub.3                                            45   t-C.sub.4 H.sub.9                                                                         CH.sub.3                                                                             NOCH.sub.3                                            46   C.sub.6 H.sub.5                                                                           CH.sub.3                                                                             NOCH.sub.3                                            47   2-ClC.sub.6 H.sub.4                                                                       CH.sub.3                                                                             NOCH.sub.3                                            48   3-ClC.sub.6 H.sub.4                                                                       CH.sub.3                                                                             NOCH.sub.3                                            49   4-ClC.sub.6 H.sub.4                                                                       CH.sub.3                                                                             NOCH.sub.3                                            50   2-CH.sub.3 C.sub.6 H.sub.4                                                                CH.sub.3                                                                             NOCH.sub.3                                            51   3-CH.sub.3 OC.sub.6 H.sub.4                                                               CH.sub.3                                                                             NOCH.sub.3                                            52   4-Cyano-C.sub.6 H.sub.4                                                                   CH.sub.3                                                                             NOCH.sub.3                                            53   2,6-F.sub.2C.sub.6 H.sub.3                                                                CH.sub.3                                                                             NOCH.sub.3                                            54   3-Pyridyl   CH.sub.3                                                                             NOCH.sub.3                                            55   2-Furyl     CH.sub.3                                                                             NOCH.sub.3                                            56   β-Naphthyl                                                                           CH.sub.3                                                                             NOCH.sub.3                                            57   CH.sub.3    C.sub.6 H.sub.5                                                                      NOCH.sub.3                                            58   C.sub.6 H.sub.5                                                                           C.sub.6 H.sub.5                                                                      NOCH.sub.3                                            59   2-CH.sub.3 C.sub.6 H.sub.4                                                                C.sub.6 H.sub.5                                                                      NOCH.sub.3                                            60   2,6-F.sub.2 C.sub.6 H.sub.3                                                               C.sub.6 H.sub.5                                                                      NOCH.sub.3                                            61   CH.sub.3    H      CHCH.sub.3                                            62   t-C.sub.4 H.sub.9                                                                         H      CHCH.sub.3                                            63   C.sub.6 H.sub.5                                                                           H      CHCH.sub.3                                            64   2-ClC.sub.6 H.sub.4                                                                       H      CHCH.sub.3                                            65   3-ClC.sub.6 H.sub.4                                                                       H      CHCH.sub.3                                            66   4-ClC.sub.6 H.sub.4                                                                       H      CHCH.sub.3                                            67   2-CH.sub.3 C.sub.6 H.sub.4                                                                H      CHCH.sub.3                                            68   3-CH.sub.3 OC.sub.6 H.sub.4                                                               H      CHCH.sub.3                                            69   4-Cyano-C.sub.6 H.sub.4                                                                   H      CHCH.sub.3                                            70   2,6-F.sub.2C.sub.6 H.sub.3                                                                H      CHCH.sub.3                                            71   3-Pyridyl   H      CHCH.sub.3                                            72   2-Furyl     H      CHCH.sub.3                                            73   β-Napththyl                                                                          H      CHCH.sub.3                                            74   CH.sub.3    CH.sub.3                                                                             CHCH.sub.3                                            75   t-C.sub.4 H.sub.9                                                                         CH.sub.3                                                                             CHCH.sub.3                                            76   C.sub.6 H.sub.5                                                                           CH.sub.3                                                                             CHCH.sub.3                                            77   2-ClC.sub.6 H.sub.4                                                                       CH.sub.3                                                                             CHCH.sub.3                                            78   3-ClC.sub.6 H.sub.4                                                                       CH.sub.3                                                                             CHCH.sub.3                                            79   4-ClC.sub.6 H.sub.4                                                                       CH.sub.3                                                                             CHCH.sub.3                                            80   2-CH.sub.3 C.sub.6 H.sub.4                                                                CH.sub.3                                                                             CHCH.sub.3                                            81   3-CH.sub.3 OC.sub.6 H.sub.4                                                               CH.sub.3                                                                             CHCH.sub.3                                            82   4-Cyano-C.sub.6 H.sub.4                                                                   CH.sub.3                                                                             CHCH.sub.3                                            83   2,6-F.sub.2C.sub.6 H.sub.3                                                                CH.sub.3                                                                             CHCH.sub.3                                            84   3-Pyridyl   CH.sub.3                                                                             CHCH.sub.3                                            85   2-Furyl     CH.sub. 3                                                                            CHCH.sub.3                                            86   β-Napththyl                                                                          CH.sub.3                                                                             CHCH.sub.3                                            87   CH.sub.3    C.sub.6 H.sub.5                                                                      CHCH.sub.3                                            88   C.sub.6 H.sub.5                                                                           C.sub.6 H.sub.5                                                                      CHCH.sub.3                                            89   2-CH.sub.3 C.sub.6 H.sub.4                                                                C.sub.6 H.sub.5                                                                      CHCH.sub.3                                            90   2,6-F.sub.2 C.sub.6 H.sub.3                                                               C.sub.6 H.sub.5                                                                      CHCH.sub.3                                            91   CH.sub.3    H      CHC.sub.2 H.sub.5                                     92   t-C.sub.4 H.sub.9                                                                         H      CHC.sub.2 H.sub.5                                     93   C.sub.6 H.sub.5                                                                           H      CHC.sub.2 H.sub.5                                     94   2-ClC.sub.6 H.sub.4                                                                       H      CHC.sub.2 H.sub.5                                     95   3-ClC.sub.6 H.sub.4                                                                       H      CHC.sub.2 H.sub.5                                     96   4-ClC.sub.6 H.sub.4                                                                       H      CHC.sub.2 H.sub.5                                     97   2-CH.sub.3 C.sub.6 H.sub.4                                                                H      CHC.sub.2 H.sub.5                                     98   3-CH.sub.3 OC.sub.6 H.sub.4                                                               H      CHC.sub.2 H.sub.5                                     99   4-Cyano-C.sub.6 H.sub.4                                                                   H      CHC.sub.2 H.sub.5                                     100  2,6-F.sub.2C.sub.6 H.sub.3                                                                H      CHC.sub.2 H.sub.5                                     101  3-Pyridyl   H      CHC.sub.2 H.sub.5                                     102  2-Furyl     H      CHC.sub.2 H.sub.5                                     103  β-Napththyl                                                                          H      CHC.sub.2 H.sub.5                                     104  CH.sub.3    CH.sub.3                                                                             CHC.sub.2 H.sub.5                                     105  t-C.sub.4 H.sub.9                                                                         CH.sub.3                                                                             CHC.sub.2 H.sub.5                                     106  C.sub.6 H.sub.5                                                                           CH.sub.3                                                                             CHC.sub.2 H.sub.5                                     107  2-ClC.sub.6 H.sub.4                                                                       CH.sub.3                                                                             CHC.sub.2 H.sub.5                                     108  3-ClC.sub.6 H.sub.4                                                                       CH.sub.3                                                                             CHC.sub.2 H.sub.5                                     109  4-ClC.sub.6 H.sub.4                                                                       CH.sub.3                                                                             CHC.sub.2 H.sub.5                                     110  2-CH.sub.3 C.sub.6 H.sub.4                                                                CH.sub.3                                                                             CHC.sub.2 H.sub.5                                     111  3-CH.sub.3 OC.sub.6 H.sub.4                                                               CH.sub.3                                                                             CHC.sub.2 H.sub.5                                     112  4-Cyano-C.sub.6 H.sub.4                                                                   CH.sub.3                                                                             CHC.sub.2 H.sub.5                                     113  2,6-F.sub.2C.sub.6 H.sub.3                                                                CH.sub.3                                                                             CHC.sub.2 H.sub.5                                     114  3-Pyridyl   CH.sub.3                                                                             CHC.sub.2 H.sub.5                                     115  2-Furyl     CH.sub.3                                                                             CHC.sub.2 H.sub.5                                     116  β-Naphthyl                                                                           CH.sub.3                                                                             CHC.sub.2 H.sub.5                                     117  CH.sub.3    C.sub.6 H.sub.5                                                                      CHC.sub.2 H.sub.5                                     118  C.sub.6 H.sub.5                                                                           C.sub.6 H.sub.5                                                                      CHC.sub.2 H.sub.5                                     119  2-CH.sub.3 C.sub.6 H.sub.4                                                                C.sub.6 H.sub.5                                                                      CHC.sub.2 H.sub.5                                     120  2,6-F.sub.2 C.sub.6 H.sub.3                                                               C.sub.6 H.sub.5                                                                      CHC.sub.2 H.sub.5                                     ______________________________________                                    

                                      TABLE VI                                    __________________________________________________________________________     ##STR16##                                                                                               Iso-                                                                              m.p.                                           No.                                                                              R           A      X    mer (°C.)                                                                       δ(CC .sub.--H)                      __________________________________________________________________________     1 H           H      CHOCH.sub.3                                              2 CH.sub.3    H      CHOCH.sub.3                                              3 C.sub.2 H.sub.5                                                                           H      CHOCH.sub.3                                              4 i-C.sub.3 H.sub.7                                                                         H      CHOCH.sub.3                                              5 t-C.sub.4 H.sub.9                                                                         H      CHOCH.sub.3                                              6 H.sub.2 CCHCH.sub.2                                                                       H      CHOCH.sub.3                                              7 H.sub.2 CCClCH.sub.2                                                                      H      CHOCH.sub.3                                              8 CH.sub.3CClCHCH.sub.2                                                                     H      CHOCH.sub.3                                              9 HCCCH.sub.2 H      CHOCH.sub.3                                              10                                                                              Cyclopropyl H      CHOCH.sub.3                                              11                                                                              C.sub.6 H.sub.5                                                                           H      CHOCH.sub.3                                              12                                                                              4-Pyridyl   H      CHOCH.sub.3                                              13                                                                              C.sub.6 H.sub. 5 CH.sub.2                                                                 H      CHOCH.sub.3                                              14                                                                              2-Pyridylmethyl                                                                           H      CHOCH.sub.3                                              15                                                                              5-Chlorothien-                                                                            H      CHOCH.sub.3                                                2-ylmethyl                                                                  16                                                                              CH.sub.3 CO H      CHOCH.sub.3                                              17                                                                              C.sub.6 H.sub.5 CO                                                                        H      CHOCH.sub.3                                              18                                                                              2-Furyl-CO  H      CHOCH.sub.3                                              19                                                                              CH.sub.3 OOCCH.sub.2                                                                      H      CHOCH.sub.3                                              20                                                                              NCCH.sub.2  H      CHOCH.sub.3                                              21                                                                              H           CH.sub.3                                                                             CHOCH.sub.3                                                                        a   oil  6.70/6.86                                                            s   oil  6.93/6.54                                  22                                                                              CH.sub.3    CH.sub.3                                                                             CHOCH.sub.3                                                                        a   oil  both 6.81                                                            s   oil  6.90/7.42                                  23                                                                              C.sub.2 H.sub.5                                                                           CH.sub.3                                                                             CHOCH.sub.3                                                                        a(80)                                                                             oil  both 6.81                                                            s(20)    6.88/7.43                                  24                                                                              i-C.sub.3 H.sub.7                                                                         CH.sub.3                                                                             CHOCH.sub.3                                                                        a   oil  both 6.80                                  25                                                                              t-C.sub.4 H.sub.9                                                                         CH.sub.3                                                                             CHOCH.sub.3                                                                        a(80)                                                                             oil  6.76/6.84                                                            s(20)                                                                             oil  6.85/7.46                                  26                                                                              H.sub.2 CCHCH.sub.2                                                                       CH.sub.3                                                                             CHOCH.sub.3                                                                        a   oil  both 6.81                                                            s   oil  6.90/7.46                                  27                                                                              H.sub.2 CCClCH.sub.2                                                                      CH.sub.3                                                                             CHOCH.sub.3                                                                        a   oil  6.75/6.87                                                            s   oil  6.92/7.47                                  28                                                                              CH.sub.3 CClCHCH.sub.2                                                                    CH.sub.3                                                                             CHOCH.sub.3                                              29                                                                              HCCCH.sub.2 CH.sub.3                                                                             CHOCH.sub.3                                              30                                                                              Cyclopropyl CH.sub.3                                                                             CHOCH.sub.3                                              31                                                                              C.sub.6 H.sub.5                                                                           CH.sub.3                                                                             CHOCH.sub.3                                              32                                                                              4-Pyridyl   CH.sub.3                                                                             CHOCH.sub.3                                              33                                                                              C.sub.6 H.sub.5 CH.sub.2                                                                  CH.sub.3                                                                             CHOCH.sub.3                                                                        a(90)                                                                             130-132                                                                   s(10)                                               34                                                                              2-Pyridylmethyl                                                                           CH.sub.3                                                                             CHOCH.sub.3                                              35                                                                              5-Chlorthien-2-                                                                           CH.sub.3                                                                             CHOCH.sub.3                                                ylmethyl                                                                    36                                                                              CH.sub.3 CO CH.sub.3                                                                             CHOCH.sub.3                                              37                                                                              C.sub.6 H.sub.5 CO                                                                        CH.sub.3                                                                             CHOCH.sub.3                                              38                                                                              2-Furyl-CO  CH.sub.3                                                                             CHOCH.sub.3                                              39                                                                              CH.sub.3 OOCCH.sub.2                                                                      CH.sub.3                                                                             CHOCH.sub.3                                              40                                                                              NCCH.sub.2  CH.sub.3                                                                             CHOCH.sub.3                                              41                                                                              H           C.sub.6 H.sub.5                                                                      CHOCH.sub.3                                              42                                                                              CH.sub.3    C.sub.6 H.sub.5                                                                      CHOCH.sub.3                                              43                                                                              C.sub.6 H.sub.5 CH.sub.2                                                                  C.sub.6 H.sub.5                                                                      CHOCH.sub.3                                              44                                                                              H.sub.2 CCClCH.sub.2                                                                      C.sub.6 H.sub.5                                                                      CHOCH.sub.3                                              45                                                                              NCCH.sub.2  C.sub.6 H.sub. 5                                                                     CHOCH.sub.3                                              46                                                                              H           p-CH.sub.3 OC.sub.6 H.sub.4                                                          CHOCH.sub.3                                              47                                                                              CH.sub.3    p-CH.sub.3 OC.sub.6 H.sub.4                                                          CHOCH.sub.3                                              48                                                                              C.sub.6 H.sub.5 CH.sub.2                                                                  p-CH.sub.3 OC.sub.6 H.sub.4                                                          CHOCH.sub.3                                              49                                                                              H.sub.2 CCClCH.sub.2                                                                      p-CH.sub.3 OC.sub.6 H.sub.4                                                          CHOCH.sub.3                                              50                                                                              NCCH.sub.2  p-CH.sub.3 OC.sub.6 H.sub.4                                                          CHOCH.sub.3                                              51                                                                              H           H      NOCH.sub.3                                                                         a   oil  6.58/6.82                                  52                                                                              CH.sub.3    H      NOCH.sub.3                                                                         a   86-88                                           53                                                                              C.sub.2 H.sub.5                                                                           H      NOCH.sub.3                                               54                                                                              i-C.sub.3 H.sub.7                                                                         H      NOCH.sub.3                                               55                                                                              t-C.sub.4 H.sub.9                                                                         H      NOCH.sub.3                                               56                                                                              H.sub.2 CCHCH.sub.2                                                                       H      NOCH.sub.3                                               57                                                                              H.sub.2 CCClCH.sub.2                                                                      H      NOCH.sub.3                                                                             oil  6.60/6.82                                                                oil  6.65/6.80                                  58                                                                              CH.sub.3CClCHCH.sub.2                                                                     H      NOCH.sub.3                                               59                                                                              HCCCH.sub.2 H      NOCH.sub.3                                               60                                                                              Cyclopropyl H      NOCH.sub.3                                               61                                                                              C.sub.6 H.sub. 5                                                                          H      NOCH.sub.3                                               62                                                                              4-Pyridyl   H      NOCH.sub.3                                               63                                                                              C.sub.6 H.sub.5 CH.sub.2                                                                  H      NOCH.sub.3                                                                         a(85)                                                                             81-83                                                                     s(15)                                               64                                                                              2-Pyridylmethyl                                                                           H      NOCH.sub.3                                               65                                                                              5-Chlorothien-                                                                            H      NOCH.sub.3                                                 2-ylmethyl                                                                  66                                                                              CH.sub.3 CO H      NOCH.sub.3                                               67                                                                              C.sub.6 H.sub.5 CO                                                                        H      NOCH.sub.3                                               68                                                                              2-Furyl-CO  H      NOCH.sub.3                                               69                                                                              CH.sub.3 OOCCH.sub.2                                                                      H      NOCH.sub.3                                               70                                                                              NCCH.sub.2  H      NOCH.sub.3                                               71                                                                              H           CH.sub.3                                                                             NOCH.sub.3                                                                         a   136-138                                                                   s   127-130                                         72                                                                              CH.sub.3    CH.sub.3                                                                             NOCH.sub.3                                                                         s   80-81                                                                              6.68/7.46                                                            a   oil                                             73                                                                              C.sub.2 H.sub.5                                                                           CH.sub.3                                                                             NOCH.sub.3                                                                         a(85)                                                                             oil  6.60/6.82                                                            s(15)    6.69/7.46                                  74                                                                              i-C.sub.3 H.sub.7                                                                         CH.sub.3                                                                             NOCH.sub.3                                                                         a   oil  6.58/6.84                                  75                                                                              t-C.sub.4 H.sub.9                                                                         CH.sub.3                                                                             NOCH.sub.3                                               76                                                                              H.sub.2 CCHCH.sub.2                                                                       CH.sub.3                                                                             NOCH.sub.3                                               77                                                                              H.sub.2 CCClCH.sub.2                                                                      CH.sub.3                                                                             NOCH.sub.3                                                                         a   oil  6.64/6.82                                                            s   oil  6.72/7.51                                  78                                                                              CH.sub.3 CClCHCH.sub.2                                                                    CH.sub.3                                                                             NOCH.sub.3                                                                         a   oil  6.61/6.81                                  79                                                                              HCCCH.sub.2 CH.sub.3                                                                             NOCH.sub.3                                               80                                                                              Cyclopropyl CH.sub.3                                                                             NOCH.sub.3                                               81                                                                              C.sub.6 H.sub.5                                                                           CH.sub.3                                                                             NCCH.sub.3                                               82                                                                              4-Pyridyl   CH.sub.3                                                                             NOCH.sub.3                                               83                                                                              C.sub.6 H.sub.5 CH.sub.2                                                                  CH.sub.3                                                                             NOCH.sub.3                                                                         a   oil  6.62/6.82                                  84                                                                              2-Pyridylmethyl                                                                           CH.sub.3                                                                             NOCH.sub.3                                               85                                                                              5-Chlorothien-                                                                            CH.sub.3                                                                             NOCH.sub.3                                                                         a   oil  6.63/6.81                                    2-ylmethyl                                                                  86                                                                              CH.sub.3 CO CH.sub.3                                                                             NOCH.sub.3                                               87                                                                              C.sub.6 H.sub.5 CO                                                                        CH.sub.3                                                                             NOCH.sub.3                                               88                                                                              2-Furyl-CO  CH.sub.3                                                                             NOCH.sub.3                                               89                                                                              CH.sub.3 OOCCH.sub.2                                                                      CH.sub.3                                                                             NOCH.sub.3                                                                         a   oil  6.65/6.80                                  90                                                                              NCCH.sub.2  CH.sub.3                                                                             NOCH.sub.3                                                                         a   81-85                                           91                                                                              H           C.sub.6 H.sub.5                                                                      NOCH.sub.3                                                                         a(70)                                                                             164-165                                                                   s(30)                                               92                                                                              CH.sub.3    C.sub.6 H.sub.5                                                                      NOCH.sub.3                                                                         a   175-179                                         93                                                                              C.sub.6 H.sub.5 CH.sub.2                                                                  C.sub.6 H.sub.5                                                                      NOCH.sub.3                                               94                                                                              H.sub.2 CCClCH.sub.2                                                                      C.sub.6 H.sub.5                                                                      NOCH.sub.3                                                95                                                                             NCCH.sub.2  C.sub.6 H.sub.5                                                                      NOCH.sub.3                                               96                                                                              H           p-CH.sub.3 OC.sub.6 H.sub.4                                                          NOCH.sub.3                                               97                                                                              CH.sub.3    p-CH.sub.3 OC.sub.6 H.sub.4                                                          NOCH.sub.3                                                                         a(40)                                                                             100-104                                                                   s(60)                                               98                                                                              C.sub.6 H.sub.5 CH.sub.2                                                                  p-CH.sub.3 OC.sub.6 H.sub.4                                                          NOCH.sub.3                                               99                                                                              H.sub.2 CCClCH.sub.2                                                                      p-CH.sub.3 OC.sub.6 H.sub.4                                                          NOCH.sub.3                                              100                                                                              NCCH.sub.2  p-CH.sub.3 OC.sub.6 H.sub.4                                                          NOCH.sub.3                                              101                                                                              H           H      CHCH.sub.3                                              102                                                                              CH.sub.3    H      CHCH.sub.3                                              103                                                                              C.sub.2 H.sub.5                                                                           H      CHCH.sub.3                                              104                                                                              i-C.sub.3 H.sub.7                                                                         H      CHCH.sub.3                                              105                                                                              t-C.sub.4 H.sub.9                                                                         H      CHCH.sub.3                                              106                                                                              H.sub.2 CCHCH.sub.2                                                                       H      CHCH.sub.3                                              107                                                                              H.sub.2 CCClCH.sub.2                                                                      H      CHCH.sub.3                                              108                                                                              CH.sub.3CClCHCH.sub.2                                                                     H      CHCH.sub.3                                              109                                                                              HCCCH.sub.2 H      CHCH.sub.3                                              110                                                                              Cyclopropyl H      CHCH.sub.3                                              111                                                                              C.sub.6 H.sub.5                                                                           H      CHCH.sub.3                                              112                                                                              4-Pyridyl   H      CHCH.sub.3                                              113                                                                              C.sub.6 H.sub.5 CH.sub.2                                                                  H      CHCH.sub.3                                              114                                                                              2-Pyridylmethyl                                                                           H      CHCH.sub.3                                              115                                                                              5-Chlorothien-                                                                            H      CHCH.sub.3                                                 2-ylmethyl                                                                 116                                                                              CH.sub.3 CO H      CHCH.sub.3                                              117                                                                              C.sub.6 H.sub.5 CO                                                                        H      CHCH.sub.3                                              118                                                                              2-Furyl-CO  H      CHCH.sub.3                                              119                                                                              CH.sub.3 OOCCH.sub.2                                                                      H      CHCH.sub.3                                              120                                                                              NCCH.sub.2  H      CHCH.sub.3                                              121                                                                              H           CH.sub.3                                                                             CHCH.sub.3                                              122                                                                              CH.sub.3    CH.sub.3                                                                             CHCH.sub.3                                              123                                                                              C.sub.2 H.sub.5                                                                           CH.sub.3                                                                             CHCH.sub.3                                              124                                                                              i-C.sub.3 H.sub.7                                                                         CH.sub.3                                                                             CHCH.sub.3                                              125                                                                              t-C.sub.4 H.sub.9                                                                         CH.sub.3                                                                             CHCH.sub.3                                              126                                                                              H.sub.2 CCHCH.sub.2                                                                       CH.sub.3                                                                             CHCH.sub.3                                              127                                                                              H.sub.2 CCClCH.sub.2                                                                      CH.sub.3                                                                             CHCH.sub.3                                              128                                                                              CH.sub.3 CClCHCH.sub.2                                                                    CH.sub.3                                                                             CHCH.sub.3                                              129                                                                              HCCCH.sub.2 CH.sub.3                                                                             CHCH.sub.3                                              130                                                                              Cyclopropyl CH.sub.3                                                                             CHCH.sub.3                                              131                                                                              C.sub.6 H.sub.5                                                                           CH.sub.3                                                                             CHCH.sub.3                                              132                                                                              4-Pyridyl   CH.sub.3                                                                             CHCH.sub.3                                              133                                                                              C.sub.6 H.sub.5 CH.sub.2                                                                  CH.sub.3                                                                             CHCH.sub.3                                              134                                                                              2-Pyridylmethyl                                                                           CH.sub.3                                                                             CHCH.sub.3                                              135                                                                              5-Chlorothien-                                                                            CH.sub.3                                                                             CHCH.sub.3                                                 2-ylmethyl                                                                 136                                                                              CH.sub.3 CO CH.sub.3                                                                             CHCH.sub.3                                              137                                                                              C.sub.6 H.sub.5 CO                                                                        CH.sub.3                                                                             CHCH.sub.3                                              138                                                                              2-Furyl-CO  CH.sub.3                                                                             CHCH.sub.3                                              139                                                                              CH.sub.3 OOCCH.sub.2                                                                      CH.sub.3                                                                             CHCH.sub.3                                              140                                                                              NCCH.sub.2  CH.sub.3                                                                             CHCH.sub.3                                              141                                                                              H           C.sub.6 H.sub.5                                                                      CHCH.sub.3                                              142                                                                              CH.sub.3    C.sub.6 H.sub.5                                                                      CHCH.sub.3                                              143                                                                              C.sub.6 H.sub.5 CH.sub.2                                                                  C.sub.6 H.sub.5                                                                      CHCH.sub.3                                              144                                                                              H.sub.2 CCClCH.sub.2                                                                      C.sub.6 H.sub.5                                                                      CHCH.sub.3                                              145                                                                              NCCH.sub.2  C.sub.6 H.sub.5                                                                      CHCH.sub.3                                              146                                                                              H           p-CH.sub.3 OC.sub.6 H.sub.4                                                          CHCH.sub.3                                              147                                                                              CH.sub.3    p-CH.sub.3 OC.sub.6 H.sub.4                                                          CHCH.sub.3                                              148                                                                              C.sub.6 H.sub.5 CH.sub.2                                                                  p-CH.sub.3 OC.sub.6 H.sub.4                                                          CHCH.sub.3                                              149                                                                              H.sub.2 CCClCH.sub.2                                                                      p-CH.sub.3 OC.sub.6 H.sub.4                                                          CHCH.sub.3                                              150                                                                              NCCH.sub.2  p-CH.sub.3 OC.sub.6 H.sub.4                                                          CHCH.sub.3                                              151                                                                              H           H      CHC.sub.2 H.sub. 5                                      152                                                                              CH.sub.3    H      CHC.sub.2 H.sub.5                                       153                                                                              C.sub.2 H.sub.5                                                                           H      CHC.sub.2 H.sub.5                                       154                                                                              i-C.sub.3 H.sub.7                                                                         H      CHC.sub.2 H.sub.5                                       155                                                                              t-C.sub.4 H.sub.9                                                                         H      CHC.sub.2 H.sub.5                                       156                                                                              H.sub.2 CCHCH.sub.2                                                                       H      CHC.sub.2 H.sub.5                                       157                                                                              H.sub.2 CCClCH.sub.2                                                                      H      CHC.sub.2 H.sub.5                                       158                                                                              CH.sub.3CClCHCH.sub.2                                                                     H      CHC.sub.2 H.sub.5                                       159                                                                              HCCCH.sub.2 H      CHC.sub.2 H.sub.5                                       160                                                                              Cyclopropyl H      CHC.sub.2 H.sub.5                                       161                                                                              C.sub.6 H.sub.5                                                                           H      CHC.sub.2 H.sub.5                                       162                                                                              4-Pyridyl   H      CHC.sub.2 H.sub.5                                       163                                                                              C.sub.6 H.sub.5 CH.sub.2                                                                  H      CHC.sub.2 H.sub.5                                       164                                                                              2-Pyridylmethyl                                                                           H      CHC.sub.2 H.sub.5                                       165                                                                              5-Chlorothien-                                                                            H      CHC.sub.2 H.sub.5                                          2-ylmethyl                                                                 166                                                                              CH.sub.3 CO H      CHC.sub.2 H.sub.5                                       167                                                                              C.sub.6 H.sub.5 CO                                                                        H      CHC.sub.2 H.sub.5                                       168                                                                              2-Furyl-CO  H      CHC.sub.2 H.sub.5                                       169                                                                              CH.sub.3 OOCCH.sub.2                                                                      H      CHC.sub.2 H.sub.5                                       170                                                                              NCCH.sub.2  H      CHC.sub.2 H.sub.5                                       171                                                                              H           CH.sub.3                                                                             CHC.sub.2 H.sub.5                                       172                                                                              CH.sub.3    CH.sub.3                                                                             CHC.sub.2 H.sub.5                                       173                                                                              C.sub.2 H.sub.5                                                                           CH.sub.3                                                                             CHC.sub.2 H.sub.5                                       174                                                                              i-C.sub.3 H.sub.7                                                                         CH.sub.3                                                                             CHC.sub.2 H.sub.5                                       175                                                                              t-C.sub.4 H.sub.9                                                                         CH.sub.3                                                                             CHC.sub.2 H.sub.5                                       176                                                                              H.sub.2 CCHCH.sub.2                                                                       CH.sub.3                                                                             CHC.sub.2 H.sub.5                                       177                                                                              H.sub.2 CCClCH.sub.2                                                                      CH.sub.3                                                                             CHC.sub.2 H.sub.5                                       178                                                                              CH.sub.3 CClCHCH.sub.2                                                                    CH.sub.3                                                                             CHC.sub.2 H.sub.5                                       179                                                                              HCCCH.sub.2 CH.sub.3                                                                             CHC.sub.2 H.sub.5                                       180                                                                              Cyclopropyl CH.sub.3                                                                             CHC.sub.2 H.sub.5                                       181                                                                              C.sub.6 H.sub.5                                                                           CH.sub.3                                                                             CHC.sub.2 H.sub.5                                       182                                                                              4-Pyridyl   CH.sub.3                                                                             CHC.sub.2 H.sub.5                                       183                                                                              C.sub.6 H.sub.5 CH.sub.2                                                                  CH.sub.3                                                                             CHC.sub.2 H.sub.5                                       184                                                                              2-Pyridylmethyl                                                                           CH.sub.3                                                                             CHC.sub.2 H.sub.5                                       185                                                                              5-Chlorothien-                                                                            CH.sub.3                                                                             CHC.sub.2 H.sub.5                                          2-ylmethyl                                                                 186                                                                              CH.sub.3 CO CH.sub.3                                                                             CHC.sub.2 H.sub.5                                       187                                                                              C.sub.6 H.sub.5 CO                                                                        CH.sub.3                                                                             CHC.sub.2 H.sub.5                                       188                                                                              2-FurylCO   CH.sub.3                                                                             CHC.sub.2 H.sub.5                                       189                                                                              CH.sub.3 OOCCH.sub.2                                                                      CH.sub.3                                                                             CHC.sub.2 H.sub.5                                       190                                                                              NCCH.sub.2  CH.sub.3                                                                             CHC.sub.2 H.sub.5                                       191                                                                              H           C.sub.6 H.sub.5                                                                      CHC.sub.2 H.sub.5                                       192                                                                              CH.sub.3    C.sub.6 H.sub.5                                                                      CHC.sub.2 H.sub.5                                       193                                                                              C.sub.6 H.sub.5 CH.sub.2                                                                  C.sub.6 H.sub.5                                                                      CHC.sub.2 H.sub.5                                       194                                                                              H.sub.2 CCClCH.sub.2                                                                      C.sub.6 H.sub.5                                                                      CHC.sub.2 H.sub.5                                       195                                                                              NCCH.sub.2  C.sub.6 H.sub.5                                                                      CHC.sub.2 H.sub.5                                       196                                                                              H           p-CH.sub.3 OC.sub.6 H.sub.4                                                          CHC.sub.2 H.sub.5                                       197                                                                              CH.sub.3    p-CH.sub.3 OC.sub.6 H.sub.4                                                          CHC.sub.2 H.sub.5                                       198                                                                              C.sub.6 H.sub.5 CH.sub.2                                                                  p-CH.sub.3 OC.sub.6 H.sub.4                                                          CHC.sub.2 H.sub.5                                       199                                                                              H.sub.2 CCClCH.sub.2                                                                      p-CH.sub.3 OC.sub.6 H.sub.4                                                          CHC.sub.2 H.sub.5                                       200                                                                              NCCH.sub.2  p-CH.sub.3 OC.sub.6 H.sub.4                                                          CHC.sub.2 H.sub.5                                       201                                                                              n-C.sub.4 H.sub.9                                                                         CH.sub.3                                                                             CHOCH.sub.3                                                                        a(90)                                                                             oil  both 6.80                                                            s(10)    6.84/7.43                                 202                                                                              2-Methylallyl                                                                             CH.sub.3                                                                             CHOCH.sub.3                                                                        a(80)                                                                             oil  both 6.81                                                            s(20)    6.92/7.50                                 203                                                                              2-Bromoallyl                                                                              CH.sub.3                                                                             CHOCH.sub.3                                                                        a(75)                                                                             oil  6.75/6.87                                                            s(25)    6.92/7.47                                 204                                                                              2-Isopropyl-                                                                              CH.sub.3                                                                             CHOCH.sub.3                                                                        a(70)                                                                             164-166                                           6-hydroxy-pyri-         s(30)                                                 midin-4-yl                                                                 205                                                                              CH.sub.3    t-C.sub.4 H.sub.9                                                                    CHOCH.sub.3                                             206                                                                              C.sub.2 H.sub.5                                                                           t-C.sub.4 H.sub.9                                                                    CHOCH.sub.3                                             207                                                                              i-C.sub.3 H.sub.7                                                                         t-C.sub.4 H.sub.9                                                                    CHOCH.sub.3                                             208                                                                              t-C.sub.4 H.sub.9                                                                         t-C.sub.4 H.sub.9                                                                    CHOCH.sub.3                                             209                                                                              2-Chloroallyl                                                                             t-C.sub.4 H.sub.9                                                                    CHOCH.sub.3                                             210                                                                              Benzyl      t-C.sub.4 H.sub.9                                                                    CHOCH.sub.3                                             211                                                                              CH.sub.3    CH.sub.3 O                                                                           CHOCH.sub.3                                             212                                                                              t-C.sub.4 H.sub.9                                                                         CH.sub.3 O                                                                           CHOCH.sub.3                                             213                                                                              2-Chloroallyl                                                                             CH.sub.3 O                                                                           CHOCH.sub.3                                             214                                                                              Benzyl      CH.sub.3 O                                                                           CHOCH.sub.3                                             215                                                                              n-C.sub.4 H.sub.9                                                                         CH.sub.3                                                                             NOCH.sub.3                                              216                                                                              2-Methylallyl                                                                             CH.sub.3                                                                             NOCH.sub.3                                                                         a(80)                                                                             oil  6.62/6.83                                                            s(20)    6.70/7.50                                 217                                                                              2-Bromoallyl                                                                              CH.sub.3                                                                             NOCH.sub.3                                                                         a(85)                                                                             oil  6.64/6.80                                                            s(15)    6.78/7.51                                 218                                                                              2-Isopropyl-                                                                              CH.sub.3                                                                             NOCH.sub.3                                                                         a(70)                                                                             176-178                                           6-hydroxy-pyri-         s(30)                                                 midin-4-yl                                                                 219                                                                              CH.sub.3    t-C.sub.4 H.sub.9                                                                    NOCH.sub.3                                                                         s   84-86                                          220                                                                              C.sub.2 H.sub.5                                                                           t-C.sub.4 H.sub.9                                                                    NOCH.sub. 3                                             221                                                                              i-C.sub.3 H.sub.7                                                                         t-C.sub.4 H.sub.9                                                                    NOCH.sub.3                                                                         s        6.59/7.40                                 222                                                                              t-C.sub.4 H.sub.9                                                                         t-C.sub.4 H.sub.9                                                                    NOCH.sub.3                                                                         s   oil  6.60/7.49                                 223                                                                              2-Chloroallyl                                                                             t-C.sub.4 H.sub.9                                                                    NOCH.sub.3                                                                         s   oil  6.60/7.22                                 224                                                                              Benzyl      t-C.sub.4 H.sub.9                                                                    NOCH.sub.3                                              225                                                                              CH.sub.3    CH.sub.3 O                                                                           NOCH.sub.3                                              226                                                                              t-C.sub.4 H.sub.9                                                                         CH.sub.3 O                                                                           NOCH.sub.3                                              227                                                                              2-Chloroallyl                                                                             CH.sub.3 O                                                                           NOCH.sub.3                                              228                                                                              Benzyl      CH.sub.3 O                                                                           NOCH.sub.3                                              __________________________________________________________________________

                                      TABLE VII                                   __________________________________________________________________________     ##STR17##                                                                                               Iso-                                                                             m.p.                                            No.                                                                              Q.sub.m        A   X    mer                                                                              (°C.)                                                                       δ (CC .sub.--H)                      __________________________________________________________________________    1  3-F            H   CHOCH.sub.3                                             2  2,6-F.sub.2    H   CHOCH.sub.3                                             3  2-Cl           H   CHOCH.sub.3                                             4  3-Cl           H   CHOCH.sub.3                                             5  4-Cl           H   CHOCH.sub.3                                             6  2,6-Cl.sub.2   H   CHOCH.sub.3                                             7  3,4-Cl.sub.2   H   CHOCH.sub.3                                             8  3-Br           H   CHOCH.sub.3                                             9  4-I            H   CHOCH.sub.3                                             10 2-Cl, 6-F      H   CHOCH.sub.3                                             11 2-CH.sub.3     H   CHOCH.sub.3                                             12 3-CH.sub.3     H   CHOCH.sub.3                                             13 4-CH.sub.3     H   CHOCH.sub.3                                             14 2,4-(CH.sub.3).sub.2                                                                         H   CHOCH.sub.3                                             15 4,6-(CH.sub.3).sub.3                                                                         H   CHOCH.sub.3                                             16 3-C.sub.2 H.sub.5                                                                            H   CHOCH.sub.3                                             17 4-t-C.sub.4 H.sub.9                                                                          H   CHOCH.sub.3                                             18 4-Cyclohexyl   H   CHOCH.sub.3                                             19 3-CH.sub.2 C.sub.6 H.sub.5                                                                   H   CHOCH.sub.3                                             20 2-OCH.sub.3    H   CHOCH.sub.3                                             21 3-OCH.sub.3    H   CHOCH.sub.3                                             22 4-OCH.sub.3    H   CHOCH.sub.3                                             23 2-O-i-C3H7     H   CHOCH.sub.3                                             24 3-OCH.sub.2 C.sub.6 H.sub.5                                                                  H   CHOCH.sub.3                                             25 3-CF.sub.3     H   CHOCH.sub.3                                             26 3-NO.sub.2     H   CHOCH.sub.3                                             27 4-NO.sub.2     H   CHOCH.sub.3                                             28 3-Cyano        H   CHOCH.sub.3                                             29 2-Cl, 4-CH.sub.3                                                                             H   CHOCH.sub.3                                             30 2-COOCH.sub.3  H   CHOCH.sub.3                                             31 4-CH.sub.2 OCH.sub.3                                                                         H   CHOCH.sub.3                                             32 4-COCH.sub.3   H   CHOCH.sub.3                                             33 2-CH.sub.3 -4-COCH.sub.3                                                                     H   CHOCH.sub.3                                             34 4-C(CH.sub.3)NOCH.sub.2 CHCH.sub.2                                                           H   CHOCH.sub.3                                             35 2-CH.sub.3 -4-C(CH.sub.3)NOCH.sub.2                                                          H   CHOCH.sub.3                                                CHCH.sub.2                                                                 36 3-F            CH.sub.3                                                                          CHOCH.sub.3                                                                        a  oil  6.77/6.83                                  37 2,6-F.sub.2    CH.sub.3                                                                          CHOCH.sub.3                                                                        a  116-118                                                                    s  180-82                                          38 2-Cl           CH.sub.3                                                                          CHOCH.sub.3                                             39 3-Cl           CH.sub.3                                                                          CHOCH.sub.3                                             40 4-Cl           CH.sub.3                                                                          CHOCH.sub.3                                             41 2,6-Cl.sub.2   CH.sub.3                                                                          CHOCH.sub.3                                                                        a  131-133                                                                    s  oil  6.85/7.38                                  42 3,4-Cl.sub.2   CH.sub.3                                                                          CHOCH.sub.3                                                                        a  oil  6.74/6.87                                  43 3-Br           CH.sub.3                                                                          CHOCH.sub.3                                                                        a  oil  6.75/6.85                                  44 4-I            CH.sub.3                                                                          CHOCH.sub.3                                             45 2-Cl, 6-F      CH.sub.3                                                                          CHOCH.sub.3                                             46 2-CH.sub.3     CH.sub.3                                                                          CHOCH.sub.3                                                                        a  oil  both 6.82                                  47 3-CH.sub.3     CH.sub.3                                                                          CHOCH.sub.3                                                                        a(75)                                                                            oil  both 6.81                                                             s(25)   6.89/7.48                                  48 4-CH.sub.3     CH.sub.3                                                                          CHOCH.sub.3                                                                        a  oil  both 6.78                                  49 2,4-(CH.sub.3).sub.2                                                                         CH.sub.3                                                                          CHOCH.sub.3                                             50 2,4,6-(CH.sub.3).sub.3                                                                       CH.sub.3                                                                          CHOCH.sub.3                                             51 3-C.sub.2 H.sub.5                                                                            CH.sub.3                                                                          CHOCH.sub.3                                             52 4-t-C.sub.4 H.sub.9                                                                          CH.sub.3                                                                          CHOCH.sub.3                                             53 4-Cyclohexyl   CH.sub.3                                                                          CHOCH.sub.3                                             54 3-CH.sub.2 C.sub.6 H.sub.5                                                                   CH.sub.3                                                                          CHOCH.sub.3                                             55 2-OCH.sub.3    CH.sub.3                                                                          CHOCH.sub.3                                             56 3-OCH.sub.3    CH.sub.3                                                                          CHOCH.sub.3                                             57 4-OCH.sub.3    CH.sub.3                                                                          CHOCH.sub.3                                             58 2-O-i-C.sub.3 H.sub.7                                                                        CH.sub.3                                                                          CHOCH.sub.3                                             59 3-OCH.sub.2 C.sub.6 H.sub.5                                                                  CH.sub.3                                                                          CHOCH.sub.3                                             60 2-CF.sub.3     CH.sub.3                                                                          CHOCH.sub.3                                                                        a  oil  6.76/6.86                                  61 3-NO.sub.2     CH.sub.3                                                                          CHOCH.sub.3                                             62 4-NO.sub.2     CH.sub.3                                                                          CHOCH.sub.3                                             63 3-Cyano        CH.sub.3                                                                          CHOCH.sub.3                                                                        a  oil  6.73/6.84                                  64 2-Cl, 4-CH.sub.3                                                                             CH.sub.3                                                                          CHOCH.sub.3                                             65 2-COOCH.sub.3  CH.sub.3                                                                          CHOCH.sub. 3                                            66 4-CH.sub.2 OCH.sub.3                                                                         CH.sub.3                                                                          CHOCH.sub.3                                             67 4-COCH.sub.3   CH.sub.3                                                                          CHOCH.sub.3                                             68 2-CH.sub.3 -4-OCH.sub.3                                                                      CH.sub.3                                                                          CHOCH.sub.3                                             69 4-C(CH.sub.3)NOCH.sub.2 CHCH.sub.2                                                           CH.sub.3                                                                          CHOCH.sub.3                                             70 2-CH.sub.3 -4-C(CH.sub.3)NOCH.sub.2                                                          CH.sub.3                                                                          CHOCH.sub.3                                                CHCH.sub.2                                                                 71 3-F            H   NOCH.sub.3                                                                         a  83-85                                           72 2,6-F.sub.2    H   NOCH.sub.3                                                                         a  120-122                                         73 2-Cl           H   NOCH.sub.3                                              74 3-Cl           H   NOCH.sub.3                                              75 4-Cl           H   NOCH.sub.3                                              76 2,6-Cl.sub.2   H   NOCH.sub.3                                                                         a(80)                                                                            127-129                                                                    s(20)                                              77 3,4-Cl.sub.2   H   NOCH.sub.3                                                                         a  oil  6.57/6.78                                  78 3-Br           H   NOCH.sub.3                                                                         a  126-128                                         79 4-I            H   NOCH.sub.3                                              80 2-Cl, 6-F      H   NOCH.sub.3                                              81 2-CH.sub.3     H   NOCH.sub.3                                              82 3-CH.sub.3     H   NOCH.sub.3                                              83 4-CH.sub.3     H   NOCH.sub.3                                                                         a  oil  6.62/6.82                                  84 2,4-(CH.sub.3).sub.2                                                                         H   NOCH.sub.3                                              85 2,4,6-(CH.sub.3).sub.3                                                                       H   NOCH.sub.3                                              86 3-C.sub.2 H.sub.5                                                                            H   NOCH.sub.3                                              87 4-t-C.sub.4 H.sub.9                                                                          H   NOCH.sub.3                                              88 4-Cyclohexyl   H   NOCH.sub.3                                              89 3-CH.sub.2 C.sub.6 H.sub.5                                                                   H   NOCH.sub.3                                              90 2-OCH.sub.3    H   NOCH.sub. 3                                             91 3-OCH.sub.3    H   NOCH.sub.3                                              92 4-OCH.sub.3    H   NOCH.sub.3                                              93 2-O-i-C.sub.3 H.sub.7                                                                        H   NOCH.sub.3                                              94 3-OCH.sub.2 C.sub.6 H.sub.5                                                                  H   NOCH.sub.3                                              95 3-CF.sub.3     H   NOCH.sub.3                                                                         a(80)                                                                            63-66                                                                      s(20)                                              96 3-NO.sub.2     H   NOCH.sub.3                                              97 4-NO.sub.2     H   NOCH.sub.3                                              98 3-Cyano        H   NOCH.sub.3                                                                         a  oil  6.58/6.78                                  99 2-Cl, 4-CH.sub.3                                                                             H   NOCH.sub.3                                              100                                                                              2-COOCH.sub.3  H   NOCH.sub.3                                              101                                                                              4-CH.sub.2 OCH.sub.3                                                                         H   NOCH.sub.3                                              102                                                                              4-COCH.sub.3   H   NOCH.sub.3                                              103                                                                              2-CH.sub.3 -4-COCH.sub.3                                                                     H   NOCH.sub.3                                              104                                                                              4-C(CH.sub.3)NOCH.sub.2 CHCH.sub.2                                                           H   NOCH.sub.3                                              105                                                                              2-CH.sub.3 -4-C(CH.sub.3)NOCH.sub.3                                                          H   NOCH.sub.3                                                 CHCH.sub.2                                                                 106                                                                              3-F            CH.sub.3                                                                          NOCH.sub.3                                                                         a  oil  6.62/6.80                                  107                                                                              2,6-F.sub.2    CH.sub.3                                                                          NOCH.sub.3                                                                         a  82-83                                                                         (Zers.)                                         108                                                                              2-Cl           CH.sub.3                                                                          NOCH.sub.3                                              109                                                                              3-Cl           CH.sub.3                                                                          NOCH.sub.3                                              110                                                                              4-Cl           CH.sub.3                                                                          NOCH.sub.3                                              111                                                                              2,6-Cl.sub.2   CH.sub.3                                                                          NOCH.sub.3                                                                         a  126-128                                         112                                                                              3,4-Cl.sub.2   CH.sub.3                                                                          NOCH.sub.3                                                                         a  oil  6.62/6.78                                  113                                                                              3-Br           CH.sub.3                                                                          NOCH.sub.3                                                                         a  oil  6.63/6.82                                  114                                                                              4-I            CH.sub.3                                                                          NOCH.sub.3                                              115                                                                              2-Cl, 6-F      CH.sub.3                                                                          NOCH.sub.3                                              116                                                                              2-CH.sub.3     CH.sub.3                                                                          NOCH.sub.3                                                                         a  oil  6.62/6.83                                  117                                                                              3-CH.sub.3     CH.sub.3                                                                          NOCH.sub.3                                                                         a(80)                                                                            oil  6.60/6.82                                                             s(20)   6.75/7.49                                  118                                                                              4-CH.sub.3     CH.sub.3                                                                          NOCH.sub.3                                              119                                                                              2,4-(CH.sub.3).sub.2                                                                         CH.sub.3                                                                          NOCH.sub.3                                              120                                                                              2,4,6-(CH.sub.3).sub.3                                                                       CH.sub.3                                                                          NOCH.sub.3                                              121                                                                              3-C.sub.2 H.sub.5                                                                            CH.sub.3                                                                          NOCH.sub.3                                              122                                                                              4-t-C.sub.4 H.sub.9                                                                          CH.sub.3                                                                          NOCH.sub.3                                              123                                                                              4-Cyclohexyl   CH.sub.3                                                                          NOCH.sub.3                                              124                                                                              3-CH.sub.2 C.sub.6 H.sub.5                                                                   CH.sub.3                                                                          NOCH.sub.3                                              125                                                                              2-OCH.sub.3    CH.sub.3                                                                          NOCH.sub.3                                              126                                                                              3-OCH.sub.3    CH.sub.3                                                                          NOCH.sub.3                                              127                                                                              4-OCH.sub.3    CH.sub.3                                                                          NOCH.sub.3                                              128                                                                              2-O-i-C.sub.3 H.sub.7                                                                        CH.sub.3                                                                          NOCH.sub.3                                              129                                                                              OCH.sub.2 C.sub.6 H.sub.5                                                                    CH.sub.3                                                                          NOCH.sub.3                                              130                                                                              3-CF.sub.3     CH.sub.3                                                                          NOCH.sub.3                                                                         a  oil  6.64/6.79                                  131                                                                              3-NO.sub.2     CH.sub.3                                                                          NOCH.sub.3                                              132                                                                              4-NO.sub.2     CH.sub.3                                                                          NOCH.sub.3                                                                            oil  6.65/6.79                                  133                                                                              3-Cyano        CH.sub.3                                                                          NOCH.sub.3                                                                            oil  6.64/6.79                                  134                                                                              2-Cl, 4-CH.sub.3                                                                             CH.sub.3                                                                          NOCH.sub.3                                              135                                                                              2-COOCH.sub.3  CH.sub.3                                                                          NOCH.sub.3                                              136                                                                              4-CH.sub.2 OCH.sub.3                                                                         CH.sub.3                                                                          NOCH.sub.3                                              137                                                                              4-COCH.sub.3   CH.sub.3                                                                          NOCH.sub.3                                              138                                                                              2-CH.sub. 3 -4-COCH.sub.3                                                                    CH.sub.3                                                                          NOCH.sub.3                                              139                                                                              4-C(CH.sub.3)NOCH.sub.2 CHCH.sub.2                                                           CH.sub.3                                                                          NOCH.sub.3                                              140                                                                              2-CH.sub.3 -4-C(CH.sub.3)NOCH.sub.2                                                          CH.sub.3                                                                          NOCH.sub.3                                                 CHCH.sub.2                                                                 141                                                                              3-F            H   CHCH.sub.3                                              142                                                                              2,6-F.sub.2    H   CHCH.sub.3                                              143                                                                              2-Cl           H   CHCH.sub.3                                              144                                                                              3-Cl           H   CHCH.sub.3                                              145                                                                              4-Cl           H   CHCH.sub.3                                              146                                                                              2,6-Cl.sub.2   H   CHCH.sub.3                                              147                                                                              3,4-Cl.sub.2   H   CHCH.sub.3                                              148                                                                              3-Br           H   CHCH.sub.3                                              149                                                                              4-I            H   CHCH.sub.3                                              150                                                                              2-Cl, 6-F      H   CHCH.sub.3                                              151                                                                              2-CH.sub.3     H   CHCH.sub.3                                              152                                                                              3-CH.sub.3     H   CHCH.sub.3                                              153                                                                              4-CH.sub.3     H   CHCH.sub.3                                              154                                                                              2,4-(CH.sub.3).sub.                                                                          H   CHCH.sub.3                                              155                                                                              2,4,6-(CH.sub.3).sub.3                                                                       H   CHCH.sub.3                                              156                                                                              3-C.sub.2 H.sub.5                                                                            H   CHCH.sub.3                                              157                                                                              4-t-C.sub.4 H.sub.9                                                                          H   CHCH.sub.3                                              158                                                                              4-Cyclohexyl   H   CHCH.sub.3                                              159                                                                              3-CH.sub.2 C.sub.6 H.sub.5                                                                   H   CHCH.sub.3                                              160                                                                              2-OCH.sub.3    H   CHCH.sub.3                                              161                                                                              3-OCH.sub.3    H   CHCH.sub.3                                              162                                                                              4-OCH.sub.3    H   CHCH.sub.3                                              163                                                                              2-O-i-C.sub.3 H.sub.7                                                                        H   CHCH.sub.3                                              164                                                                              3-OCH.sub.2 C.sub.6 H.sub.5                                                                  H   CHCH.sub.3                                              165                                                                              3-CF.sub.3     H   CHCH.sub.3                                              166                                                                              3-NO.sub.2     H   CHCH.sub.3                                              167                                                                              4-NO.sub.2     H   CHCH.sub.3                                              168                                                                              3-Cyano        H   CHCH.sub.3                                              169                                                                              2-Cl, 4-CH.sub.3                                                                             H   CHCH.sub.3                                              170                                                                              2-COOCH.sub.3  H   CHCH.sub.3                                              171                                                                              4-CH.sub.2 CCH.sub.3                                                                         H   CHCH.sub.3                                              172                                                                              4-COCH.sub.3   H   CHCH.sub.3                                              173                                                                              2-CH.sub.3 -4-COCH.sub.3                                                                     H   CHCH.sub.3                                              174                                                                              4-C(CH.sub.3)NOCH.sub.2 CHCH.sub.2                                                           H   CHCH.sub.3                                              175                                                                              2-CH.sub.3 -4-C(CH.sub.3)NOCH.sub.2                                                          H   CHCH.sub.3                                                 CHCH.sub.2                                                                 176                                                                              3-F            CH.sub.3                                                                          CHCH.sub.3                                              177                                                                              2,6-F.sub.2    CH.sub.3                                                                          CHCH.sub.3                                              178                                                                              2-Cl           CH.sub.3                                                                          CHCH.sub.3                                              179                                                                              3-Cl           CH.sub.3                                                                          CHCH.sub.3                                              180                                                                              4-Cl           CH.sub.3                                                                          CHCH.sub.3                                              181                                                                              2,6-Cl.sub.2   CH.sub.3                                                                          CHCH.sub.3                                              182                                                                              3,4-Cl.sub.2   CH.sub.3                                                                          CHCH.sub.3                                              183                                                                              3-Br           CH.sub.3                                                                          CHCH.sub.3                                              184                                                                              4-I            CH.sub.3                                                                          CHCH.sub.3                                              185                                                                              2-Cl, 6-F      CH.sub.3                                                                          CHCH.sub.3                                              186                                                                              2-CH.sub.3     CH.sub.3                                                                          CHCH.sub.3                                              187                                                                              3-CH.sub.3     CH.sub.3                                                                          CHCH.sub.3                                              188                                                                              4-CH.sub.3     CH.sub.3                                                                          CHCH.sub.3                                              189                                                                              2,4-(CH.sub.3).sub.2                                                                         CH.sub.3                                                                          CHCH.sub.3                                              190                                                                              2,4,6-(CH.sub.3).sub.3                                                                       CH.sub.3                                                                          CHCH.sub.3                                              191                                                                              3-C.sub.2 H.sub.5                                                                            CH.sub.3                                                                          CHCH.sub.3                                              192                                                                              4-t-C.sub.4 H.sub.9                                                                          CH.sub.3                                                                          CHCH.sub.3                                              193                                                                              4-Cyclohexyl   CH.sub.3                                                                          CHCH.sub.3                                              194                                                                              3-CH.sub.2 C.sub.6 H.sub.5                                                                   CH.sub.3                                                                          CHCH.sub.3                                              195                                                                              2-OCH.sub.3    CH.sub.3                                                                          CHCH.sub.3                                              196                                                                              3-OCH.sub.3    CH.sub.3                                                                          CHCH.sub.3                                              197                                                                              4-OCH.sub.3    CH.sub.3                                                                          CHCH.sub.3                                              198                                                                              2-O-i-C.sub.3 H.sub.7                                                                        CH.sub.3                                                                          CHCH.sub.3                                              199                                                                              3-OCH.sub.2 C.sub.6 H.sub.5                                                                  CH.sub.3                                                                          CHCH.sub.3                                              200                                                                              3-CF.sub.3     CH.sub.3                                                                          CHCH.sub.3                                              201                                                                              3-NO.sub.2     CH.sub.3                                                                          CHCH.sub.3                                              202                                                                              4-NO.sub.2     CH.sub.3                                                                          CHCH.sub.3                                              203                                                                              3-Cyano        CH.sub.3                                                                          CHCH.sub.3                                              204                                                                              2-Cl, 4-CH.sub.3                                                                             CH.sub.3                                                                          CHCH.sub.3                                              205                                                                              2-COOCH.sub.3  CH.sub.3                                                                          CHCH.sub.3                                              206                                                                              4-CH.sub.2 OCH.sub.3                                                                         CH.sub.3                                                                          CHCH.sub.3                                              207                                                                              4-COCH.sub.3   CH.sub.3                                                                          CHCH.sub.3                                              208                                                                              2-CH.sub.3 -4-COCH.sub.3                                                                     CH.sub.3                                                                          CHCH.sub.3                                              209                                                                              4-C(CH.sub.3)NOCH.sub.2 CHCH.sub.2                                                           CH.sub.3                                                                          CHCH.sub.3                                              210                                                                              2-CH.sub.3 -4-C(CH.sub.3)NOCH.sub.2                                                          CH.sub.3                                                                          CHCH.sub.3                                                 CHCH.sub.2                                                                 211                                                                              3-F            H   CHC.sub.2 H.sub.5                                       212                                                                              2,6-F.sub.2    H   CHC.sub.2 H.sub.5                                       213                                                                              2-Cl           H   CHC.sub.2 H.sub.5                                       214                                                                              3-Cl           H   CHC.sub.2 H.sub.5                                       215                                                                              4-Cl           H   CHC.sub.2 H.sub.5                                       216                                                                              2,6-Cl.sub.2   H   CHC.sub.2 H.sub.5                                       217                                                                              3,4-Cl.sub.2   H   CHC.sub.2 H.sub.5                                       218                                                                              3-Br           H   CHC.sub.2 H.sub.5                                       219                                                                              4-I            H   CHC.sub.2 H.sub.5                                       220                                                                              2-Cl, 6-F      H   CHC.sub.2 H.sub.5                                       221                                                                              2-CH.sub.3     H   CHC.sub.2 H.sub.5                                       222                                                                              3-CH.sub.3     H   CHC.sub.2 H.sub.5                                       223                                                                              4-CH.sub.3     H   CHC.sub.2 H.sub.5                                       224                                                                              2,4-(CH.sub.3).sub.2                                                                         H   CHC.sub.2 H.sub.5                                       225                                                                              2,4,6-(CH.sub.3).sub.3                                                                       H   CHC.sub.2 H.sub.5                                       226                                                                              3-C.sub.2 H.sub.5                                                                            H   CHC.sub.2 H.sub.5                                       227                                                                              4-t-C.sub.4 H.sub.9                                                                          H   CHC.sub.2 H.sub.5                                       228                                                                              4-Cyclohexyl   H   CHC.sub.2 H.sub.5                                       229                                                                              3-CH.sub.2 C.sub.6 H.sub.5                                                                   H   CHC.sub.2 H.sub.5                                       230                                                                              2-OCH.sub.3    H   CHC.sub.2 H.sub.5                                       231                                                                              3-OCH.sub.3    H   CHC.sub.2 H.sub.5                                       232                                                                              4-OCH.sub.3    H   CHC.sub.2 H.sub.5                                       233                                                                              2-O-i-C.sub.3 H.sub.7                                                                        H   CHC.sub.2 H.sub.5                                       234                                                                              3-OCH.sub.2 C.sub.6 H.sub.5                                                                  H   CHC.sub.2 H.sub.5                                       235                                                                              3-CF.sub.3     H   CHC.sub.2 H.sub.5                                       236                                                                              3-NO.sub.2     H   CHC.sub.2 H.sub.5                                       237                                                                              4-NO.sub.2     H   CHC.sub.2 H.sub.5                                       238                                                                              3-Cyano        H   CHC.sub.2 H.sub.5                                       239                                                                              2-Cl, 4-CH.sub.3                                                                             H   CHC.sub.3 H.sub.5                                       240                                                                              2-COOCH.sub.3  H   CHC.sub.2 H.sub.5                                       241                                                                              4-CH.sub.2 OCH.sub.3                                                                         H   CHC.sub.2 H.sub.5                                       242                                                                              4-COCH.sub.3   H   CHC.sub.2 H.sub.5                                       243                                                                              2-CH.sub.3 -4-COCH.sub.3                                                                     H   CHC.sub.2 H.sub.5                                       244                                                                              4-C(CH.sub.3)NOCH.sub.2 CHCH.sub.2                                                           H   CHC.sub.2 H.sub.5                                       245                                                                              2-CH.sub.3 -4-C(CH.sub.3)NOCH.sub.2                                                          H   CHC.sub.2 H.sub.5                                          CHCH.sub.2                                                                 246                                                                              3-F            CH.sub.3                                                                          CHC.sub.2 H.sub.5                                       247                                                                              2,6-F.sub.2    CH.sub.3                                                                          CHC.sub.2 H.sub.5                                       248                                                                              2-Cl           CH.sub.3                                                                          CHC.sub.2 H.sub.5                                       249                                                                              3-Cl           CH.sub.3                                                                          CHC.sub.2 H.sub.5                                       250                                                                              4-Cl           CH.sub.3                                                                          CHC.sub.2 H.sub.5                                       251                                                                              2,6-Cl.sub.2   CH.sub.3                                                                          CHC.sub.2 H.sub.5                                       252                                                                              3,4-Cl.sub.2   CH.sub.3                                                                          CHC.sub.2 H.sub.5                                       253                                                                              3-Br           CH.sub.3                                                                          CHC.sub.2 H.sub.5                                       254                                                                              4-I            CH.sub.3                                                                          CHC.sub.2 H.sub.5                                       255                                                                              2-Cl, 6-F      CH.sub.3                                                                          CHC.sub.2 H.sub.5                                       256                                                                              2-CH.sub.3     CH.sub.3                                                                          CHC.sub.2 H.sub.5                                       257                                                                              3-CH.sub.3     CH.sub.3                                                                          CHC.sub.2 H.sub.5                                       258                                                                              4-CH.sub.3     CH.sub.3                                                                          CHC.sub.2 H.sub.5                                       259                                                                              2,4-(CH.sub.3).sub.2                                                                         CH.sub.3                                                                          CHC.sub.2 H.sub.5                                       260                                                                              2,4,6-(CH.sub.3).sub.3                                                                       CH.sub.3                                                                          CHC.sub.2 H.sub.5                                       261                                                                              3-C.sub.2 H.sub.5                                                                            CH.sub. 3                                                                         CHC.sub.2 H.sub.5                                       262                                                                              4-t-C.sub.4 H.sub.9                                                                          CH.sub.3                                                                          CHC.sub.2 H.sub.5                                       263                                                                              4-Cyclohexyl   CH.sub.3                                                                          CHC.sub.2 H.sub.5                                       264                                                                              3-CH.sub.2 C.sub.6 H.sub.5                                                                   CH.sub.3                                                                          CHC.sub.2 H.sub.5                                       265                                                                              2-OCH.sub.3    CH.sub.3                                                                          CHC.sub.2 H.sub.5                                       266                                                                              3-OCH.sub.3    CH.sub.3                                                                          CHC.sub.2 H.sub.5                                       267                                                                              4-OCH.sub.3    CH.sub.3                                                                          CHC.sub.2 H.sub.5                                       268                                                                              2-O-i-C.sub.3 H.sub.7                                                                        CH.sub.3                                                                          CHC.sub.2 H.sub.5                                       269                                                                              3-OCH.sub.2 C.sub.6 H.sub.5                                                                  CH.sub.3                                                                          CHC.sub.2 H.sub.5                                       270                                                                              3-CF.sub.3     CH.sub.3                                                                          CHC.sub.2 H.sub.5                                       271                                                                              3-NO.sub.2     CH.sub.3                                                                          CHC.sub.2 H.sub.5                                       272                                                                              4-NO.sub.2     CH.sub.3                                                                          CHC.sub.2 H.sub.5                                       273                                                                              3-Cyano        CH.sub.3                                                                          CHC.sub.2 H.sub.5                                       274                                                                              2-Cl, 4-CH.sub.3                                                                             CH.sub.3                                                                          CHC.sub.2 H.sub.5                                       275                                                                              2-COOCH.sub.3  CH.sub.3                                                                          CHC.sub.2 H.sub.5                                       276                                                                              4-CH.sub.2 OCH.sub.3                                                                         CH.sub.3                                                                          CHC.sub.2 H.sub.5                                       277                                                                              4-COCH.sub.3   CH.sub.3                                                                          CHC.sub.2 H.sub.5                                       278                                                                              2-CH.sub.3 -4-COCH.sub.3                                                                     CH.sub.3                                                                          CHC.sub.2 H.sub.5                                       279                                                                              4-C(CH.sub.3)NOCH.sub.2 CHCH.sub.2                                                           CH.sub.3                                                                          CHC.sub.2 H.sub.5                                       280                                                                              2-CH.sub.3 -4-C(CH.sub.3)NOCH.sub.2                                                          CH.sub.3                                                       CH CH.sub.2                                                                281                                                                              4-F            CH.sub.3                                                                          CHOCH.sub.3                                                                        a  oil  6.76/6.83                                  282                                                                              2-OCH.sub.3    t-C.sub.4 H.sub.9                                                                 CHOCH.sub.3                                             283                                                                              3-F            t-C.sub.4 H.sub.9                                                                 CHOCH.sub.3                                             284                                                                              4-CH.sub.3     t-C.sub.4 H.sub.9                                                                 CHOCH.sub.3                                             285                                                                              3,5-Cl.sub.2   t-C.sub.4 H.sub.9                                                                 CHOCH.sub.3                                             286                                                                              2-OCH.sub.3    CH.sub.3 O                                                                        CHOCH.sub.3                                             287                                                                              3-CF.sub.3     CH.sub.3 O                                                                        CHOCH.sub.3                                             288                                                                              4-CH.sub.3     CH.sub.3 O                                                                        CHOCH.sub.3                                             289                                                                              3,5-Cl.sub.2   CH.sub.3 O                                                                        CHOCH.sub.3                                             290                                                                              4-F            CH.sub.3                                                                          NOCH.sub.3                                                                         a  oil  6.62/6.80                                  291                                                                              2-OCH.sub.3    t-C.sub.4 H.sub.9                                                                 NOCH.sub.3                                              292                                                                              3-F            t-C.sub.4 H.sub.9                                                                 NOCH.sub.3                                                                         s  oil  6.4/7.44                                   293                                                                              4-CH.sub.3     t-C.sub.4 H.sub.9                                                                 NOCH.sub.3                                              294                                                                              3,5-Cl.sub.2   t-C.sub.4 H.sub.9                                                                 NOCH.sub.3                                              295                                                                              2-OCH.sub.3    CH.sub.3 O                                                                        NOCH.sub.3                                              296                                                                              3-CF.sub.3     CH.sub.3 O                                                                        NOCH.sub.3                                              297                                                                              4-CH.sub.3     CH.sub.3 O                                                                        NOCH.sub.3                                              298                                                                              3,5-Cl.sub.2   CH.sub.3 O                                                                        NOCH.sub.3                                              __________________________________________________________________________

                                      TABLE VIII                                  __________________________________________________________________________     ##STR18##                                                                                             Iso-                                                                             m.p.                                              No. R        R' A   X    mer                                                                              (°C.)                                                                        δ (CC .sub.-- H)                      __________________________________________________________________________    1   H        H  H   CHOCH.sub.3                                               2   CH.sub.3 H  H   CHOCH.sub.3                                               3   t-C.sub.4 H.sub.9                                                                      H  H   CHOCH.sub.3                                               4   C.sub.6 H.sub.5                                                                        H  H   CHOCH.sub.3                                               5   2-ClC.sub.6 H.sub.4                                                                    H  H   CHOCH.sub.3                                               6   3-NO.sub.2 C.sub.6 H.sub.4                                                             H  H   CHOCH.sub.3                                               7   4-CH.sub.3 OC.sub.6 H.sub.4                                                            H  H   CHOCH.sub.3                                               8   C.sub.6 H.sub.5 CH.sub.2                                                               H  H   CHOCH.sub.3                                               9   2-ClC.sub.6 H.sub.4 CH.sub.2                                                           H  H   CHOCH.sub.3                                               10  3-NO.sub.2 C.sub.6 H.sub.4 CH.sub.2                                                    H  H   CHOCH.sub.3                                               11  4-CH.sub.3 OC.sub.6 H.sub.4 CH.sub.2                                                   H  H   CHOCH.sub.3                                               12  CH.sub.3 CO                                                                            H  H   CHOCH.sub.3                                               13  C.sub.6 H.sub.5 CO                                                                     H  H   CHOCH.sub.3                                               14  CH.sub.3 CH.sub.3                                                                         H   CHOCH.sub.3                                               15  C.sub.6 H.sub.5                                                                        CH.sub.3                                                                         H   CHOCH.sub.3                                               16  C.sub.6 H.sub.5 CH.sub.2                                                               CH.sub.3                                                                         H   CHOCH.sub.3                                               17  CH.sub.3 CO                                                                            CH.sub.3                                                                         H   CHOCH.sub.3                                               18  C.sub.6 H.sub.5 CO                                                                     CH.sub.3                                                                         H   CHOCH.sub.3                                               19  H        H  CH.sub.3                                                                          CHOCH.sub.3                                               20  CH.sub.3 H  CH.sub.3                                                                          CHOCH.sub.3                                               21  t-C.sub.4 H.sub.9                                                                      H  CH.sub.3                                                                          CHOCH.sub.3                                               22  C.sub.6 H.sub.5                                                                        H  CH.sub.3                                                                          CHOCH.sub.3                                               23  2-Cl-C.sub.6 H.sub.4                                                                   H  CH.sub.3                                                                          CHOCH.sub.3                                               24  3-NO.sub.2C.sub.6 H.sub.4                                                              H  CH.sub.3                                                                          CHOCH.sub.3                                               25  4-CH.sub.3 OC.sub.6 H.sub.4                                                            H  CH.sub.3                                                                          CHOCH.sub.3                                               26  C.sub.6 H.sub.5 CH.sub.2                                                               H  CH.sub.3                                                                          CHOCH.sub.3                                               27  2-ClC.sub.6 H.sub.4 CH.sub.2                                                           H  CH.sub.3                                                                          CHOCH.sub.3                                               28  3-NO.sub.2 C.sub.6 H.sub.4 CH.sub.2                                                    H  CH.sub.3                                                                          CHOCH.sub.3                                               29  4-CH.sub.3 OC.sub.6 H.sub.4 CH.sub.2                                                   H  CH.sub.3                                                                          CHOCH.sub.3                                               30  CH.sub.3 CO                                                                            H  CH.sub.3                                                                          CHOCH.sub.3                                               31  C.sub.6 H.sub.5 CO                                                                     H  CH.sub.3                                                                          CHOCH.sub.3                                               32  CH.sub.3 CH.sub.3                                                                         CH.sub.3                                                                          CHOCH.sub.3                                               33  C.sub.6 H.sub.5                                                                        CH.sub.3                                                                         CH.sub.3                                                                          CHOCH.sub.3                                               34  C.sub.6 H.sub.5 CH.sub.2                                                               CH.sub.3                                                                         CH.sub.3                                                                          CHOCH.sub.3                                               35  CH.sub.3 CO                                                                            CH.sub.3                                                                         CH.sub.3                                                                          CHOCH.sub.3                                               36  C.sub.6 H.sub.5 CO                                                                     CH.sub.3                                                                         CH.sub.3                                                                          CHOCH.sub.3                                               37  CH.sub.3 H  C.sub.6 H.sub.5                                                                   CHOCH.sub.3                                               38  C.sub.6 H.sub.5                                                                        H  C.sub.6 H.sub.5                                                                   CHOCH.sub.3                                               39  C.sub.6 H.sub.5 CH.sub.2                                                               H  C.sub.6 H.sub.5                                                                   CHOCH.sub.3                                               40  CH.sub.3 CO                                                                            H  C.sub.6 H.sub.5                                                                   CHOCH.sub.3                                               41  C.sub.6 H.sub.5 CO                                                                     H  C.sub.6 H.sub.5                                                                   CHOCH.sub.3                                               42  CH.sub.3 CH.sub.3                                                                         C.sub.6 H.sub.5                                                                   CHOCH.sub.3                                               43  C.sub.6 H.sub.5                                                                        CH.sub.3                                                                         C.sub.6 H.sub.5                                                                   CHOCH.sub.3                                               44  C.sub.6 H.sub.5 CH.sub.2                                                               CH.sub.3                                                                         C.sub.6 H.sub.5                                                                   CHOCH.sub.3                                               45  CH.sub.3 CO                                                                            CH.sub.3                                                                         C.sub.6 H.sub.5                                                                   CHOCH.sub.3                                               46  C.sub.6 H.sub.5 CO                                                                     CH.sub.3                                                                         C.sub.6 H.sub.5                                                                   CHOCH.sub.3                                               47  H        H  H   NOCH.sub.3                                                48  CH.sub.3 H  H   NOCH.sub.3                                                49  t-C.sub.4 H.sub.9                                                                      H  H   NOCH.sub.3                                                50  C.sub.6 H.sub.5                                                                        H  H   NOCH.sub.3                                                51  2-ClC.sub.6 H.sub.4                                                                    H  H   NOCH.sub.3                                                52  3-NO.sub.2 C.sub.6 H.sub.4                                                             H  H   NOCH.sub.3                                                53  4-CH.sub.3 OC.sub.6 H.sub.4                                                            H  H   NOCH.sub.3                                                54  C.sub.6 H.sub.5 CH.sub.2                                                               H  H   NOCH.sub.3                                                55  2-ClC.sub.6 H.sub.4 CH.sub.2                                                           H  H   NOCH.sub.3                                                56  3-NO.sub.2 C.sub.6 H.sub.4 CH.sub.2                                                    H  H   NOCH.sub.3                                                57  4-CH.sub.3 OC.sub.6 H.sub.4 CH.sub.2                                                   H  H   NOCH.sub.3                                                58  CH.sub.3 CO                                                                            H  H   NOCH.sub.3                                                59  C.sub.6 H.sub.5 CO                                                                     H  H   NOCH.sub.3                                                60  CH.sub.3 CH.sub.3                                                                         H   NOCH.sub.3                                                61  C.sub.6 H.sub.5                                                                        CH.sub.3                                                                         H   NOCH.sub.3                                                62  C.sub.6 H.sub.5 CH.sub.2                                                               CH.sub.3                                                                         H   NOCH.sub.3                                                63  CH.sub.3 CO                                                                            CH.sub.3                                                                         H   NOCH.sub.3                                                64  C.sub.6 H.sub.5 CO                                                                     CH.sub.3                                                                         H   NOCH.sub.3                                                65  H        H  CH.sub.3                                                                          NOCH.sub.3                                                66  CH.sub.3 H  CH.sub.3                                                                          NOCH.sub.3                                                67  t-C.sub.4 H.sub.9                                                                      H  CH.sub.3                                                                          NOCH.sub.3                                                68  C.sub.6 H.sub.5                                                                        H  CH.sub.3                                                                          NOCH.sub.3                                                                         a  155-158                                           69  2-Cl-C.sub.6 H.sub.4                                                                   H  CH.sub.3                                                                          NOCH.sub.3                                                70  3-NO.sub.2C.sub.6 H.sub.4                                                              H  CH.sub.3                                                                          NOCH.sub.3                                                                         a  170                                                                           (de-                                                                          comp.)                                            71  4-CH.sub.3 OC.sub.6 H.sub.4                                                            H  CH.sub.3                                                                          NOCH.sub.3                                                72  C.sub.6 H.sub.5 CH.sub.2                                                               H  CH.sub.3                                                                          NOCH.sub.3                                                73  2-ClC.sub.6 H.sub.4 CH.sub.2                                                           H  CH.sub.3                                                                          NOCH.sub.3                                                74  3-NO.sub.2 C.sub.6 H.sub.4 CH.sub.2                                                    H  CH.sub.3                                                                          NOCH.sub.3                                                75  4-CH.sub.3 OC.sub.6 H.sub.4 CH.sub.2                                                   H  CH.sub.3                                                                          NOCH.sub.3                                                76  CH.sub.3 CO                                                                            H  CH.sub.3                                                                          NOCH.sub.3                                                77  C.sub.6 H.sub.5 CO                                                                     H  CH.sub.3                                                                          NOCH.sub.3                                                78  CH.sub.3 CH.sub.3                                                                         CH.sub.3                                                                          NOCH.sub.3                                                79  C.sub.6 H.sub.5                                                                        CH.sub.3                                                                         CH.sub.3                                                                          NOCH.sub.3                                                80  C.sub.6 H.sub.5 CH.sub.2                                                               CH.sub.3                                                                         CH.sub.3                                                                          NOCH.sub.3                                                81  CH.sub.3 CO                                                                            CH.sub.3                                                                         CH.sub.3                                                                          NOCH.sub.3                                                82  C.sub.6 H.sub.5 CO                                                                     CH.sub.3                                                                         CH.sub.3                                                                          NOCH.sub.3                                                83  CH.sub.3 H  C.sub.6 H.sub.5                                                                   NOCH.sub.3                                                                         s  oil   6.57/7.52                                   84  C.sub.6 H.sub.5                                                                        H  C.sub.6 H.sub.5                                                                   NOCH.sub.3                                                85  C.sub.6 H.sub.5 CH.sub.2                                                               H  C.sub.6 H.sub.5                                                                   NOCH.sub.3                                                86  CH.sub.3 CO                                                                            H  C.sub.6 H.sub.5                                                                   NOCH.sub.3                                                87  C.sub.6 H.sub.5 CO                                                                     H  C.sub.6 H.sub.5                                                                   NOCH.sub.3                                                88  CH.sub.3 CH.sub.3                                                                         C.sub.6 H.sub.5                                                                   NOCH.sub.3                                                89  C.sub.6 H.sub.5                                                                        CH.sub.3                                                                         C.sub.6 H.sub.5                                                                   NOCH.sub.3                                                90  C.sub.6 H.sub.5 CH.sub.2                                                               CH.sub.3                                                                         C.sub.6 H.sub.5                                                                   NOCH.sub.3                                                91  CH.sub.3 CO                                                                            CH.sub.3                                                                         C.sub.6 H.sub.5                                                                   NOCH.sub.3                                                92  C.sub.6 H.sub.5 CO                                                                     CH.sub.3                                                                         C.sub.6 H.sub.5                                                                   NOCH.sub.3                                                93  H        H  H   CHCH.sub.3                                                94  CH.sub.3 H  H   CHCH.sub.3                                                95  t-C.sub.4 H.sub.9                                                                      H  H   CHCH.sub.3                                                96  C.sub.6 H.sub.5                                                                        H  H   CHCH.sub.3                                                97  2-ClC.sub.6 H.sub.4                                                                    H  H   CHCH.sub.3                                                98  3-NO.sub.2 C.sub.6 H.sub.4                                                             H  H   CHCH.sub.3                                                99  4-CH.sub.3 OC.sub.6 H.sub.4                                                            H  H   CHCH.sub.3                                                100 C.sub.6 H.sub.5 CH.sub. 2                                                              H  H   CHCH.sub.3                                                101 2-ClC.sub.6 H.sub.4 CH.sub.2                                                           H  H   CHCH.sub.3                                                102 3-NO.sub.2 C.sub.6 H.sub.4 CH.sub.2                                                    H  H   CHCH.sub.3                                                103 4-CH.sub.3 OC.sub.6 H.sub.4 CH.sub.2                                                   H  H   CHCH.sub.3                                                104 CH.sub.3 CO                                                                            H  H   CHCH.sub.3                                                105 C.sub.6 H.sub.5 CO                                                                     H  H   CHCH.sub.3                                                106 CH.sub.3 CH.sub.3                                                                         H   CHCH.sub.3                                                107 C.sub.6 H.sub.5                                                                        CH.sub.3                                                                         H   CHCH.sub.3                                                108 C.sub.6 H.sub.5 CH.sub.2                                                               CH.sub.3                                                                         H   CHCH.sub.3                                                109 CH.sub.3 CO                                                                            CH.sub.3                                                                         H   CHCH.sub.3                                                110 C.sub.6 H.sub.5 CO                                                                     CH.sub.3                                                                         H   CHCH.sub.3                                                111 H        H  CH.sub.3                                                                          CHCH.sub.3                                                112 CH.sub.3 H  CH.sub.3                                                                          CHCH.sub.3                                                113 t-C.sub.4 H.sub.9                                                                      H  CH.sub.3                                                                          CHCH.sub.3                                                114 C.sub.6 H.sub.5                                                                        H  CH.sub.3                                                                          CHCH.sub.3                                                115 2-Cl-C.sub.6 H.sub.4                                                                   H  CH.sub.3                                                                          CHCH.sub.3                                                116 3-NO.sub.2C.sub.6 H.sub.4                                                              H  CH.sub.3                                                                          CHCH.sub.3                                                117 4-CH.sub.3 OC.sub.6 H.sub.4                                                            H  CH.sub.3                                                                          CHCH.sub.3                                                118 C.sub.6 H.sub.5 CH.sub.2                                                               H  CH.sub.3                                                                          CHCH.sub.3                                                119 2-ClC.sub.6 H.sub.4 CH.sub.2                                                           H  CH.sub.3                                                                          CHCH.sub.3                                                120 3-NO.sub.2 C.sub.6 H.sub.4 CH.sub.2                                                    H  CH.sub.3                                                                          CHCH.sub.3                                                121 4-CH.sub.3 OC.sub.6 H.sub.4 CH.sub.2                                                   H  CH.sub.3                                                                          CHCH.sub.3                                                122 CH.sub.3 CO                                                                            H  CH.sub.3                                                                          CHCH.sub.3                                                123 C.sub.6 H.sub.5 CO                                                                     H  CH.sub.3                                                                          CHCH.sub.3                                                124 CH.sub.3 CH.sub.3                                                                         CH.sub.3                                                                          CHCH.sub.3                                                125 C.sub.6 H.sub.5                                                                        CH.sub.3                                                                         CH.sub.3                                                                          CHCH.sub.3                                                126 C.sub.6 H.sub.5 CH.sub.2                                                               CH.sub.3                                                                         CH.sub.3                                                                          CHCH.sub.3                                                127 CH.sub.3 CO                                                                            CH.sub.3                                                                         CH.sub.3                                                                          CHCH.sub.3                                                128 C.sub.6 H.sub.5 CO                                                                     CH.sub.3                                                                         CH.sub.3                                                                          CHCH.sub.3                                                129 CH.sub.3 H  C.sub.6 H.sub.5                                                                   CHCH.sub.3                                                130 C.sub.6 H.sub.5                                                                        H  C.sub.6 H.sub.5                                                                   CHCH.sub.3                                                131 C.sub.6 H.sub.5 CH.sub.2                                                               H  C.sub.6 H.sub.5                                                                   CHCH.sub.3                                                132 CH.sub.3 CO                                                                            H  C.sub.6 H.sub.5                                                                   CHCH.sub.3                                                133 C.sub.6 H.sub.5 CO                                                                     H  C.sub.6 H.sub.5                                                                   CHCH.sub.3                                                134 CH.sub.3 CH.sub.3                                                                         C.sub.6 H.sub.5                                                                   CHCH.sub.3                                                135 C.sub.6 H.sub.5                                                                        CH.sub.3                                                                         C.sub.6 H.sub.5                                                                   CHCH.sub.3                                                136 C.sub.6 H.sub.5 CH.sub.2                                                               CH.sub.3                                                                         C.sub.6 H.sub.5                                                                   CHCH.sub.3                                                137 CH.sub.3 CO                                                                            CH.sub.3                                                                         C.sub.6 H.sub.5                                                                   CHCH.sub.3                                                138 C.sub.6 H.sub.5 CO                                                                     CH.sub.3                                                                         C.sub.6 H.sub.5                                                                   CHCH.sub.3                                                139 H        H  H   CHC.sub.2 H.sub.5                                         140 CH.sub.3 H  H   CHC.sub.2 H.sub.5                                         141 t-C.sub.4 H.sub.9                                                                      H  H   CHC.sub.2 H.sub.5                                         142 C.sub.6 H.sub.5                                                                        H  H   CHC.sub.2 H.sub.5                                         143 2-ClC.sub.6 H.sub.4                                                                    H  H   CHC.sub.2 H.sub.5                                         144 3-NO.sub.2 C.sub.6 H.sub.4                                                             H  H   CHC.sub.2 H.sub.5                                         145 4-CH.sub.3 OC.sub.6 H.sub.4                                                            H  H   CHC.sub.2 H.sub.5                                         146 C.sub.6 H.sub.5 CH.sub.2                                                               H  H   CHC.sub.2 H.sub.5                                         147 2-ClC.sub.6 H.sub.4 CH.sub.2                                                           H  H   CHC.sub.2 H.sub.5                                         148 3-NO.sub.2 C.sub.6 H.sub.4 CH.sub.2                                                    H  H   CHC.sub.2 H.sub.5                                         149 4-CH.sub.3 OC.sub.6 H.sub.4 CH.sub.2                                                   H  H   CHC.sub.2 H.sub.5                                         150 CH.sub.3 CO                                                                            H  H   CHC.sub.2 H.sub.5                                         151 C.sub.6 H.sub.5 CO                                                                     H  H   CHC.sub.2 H.sub.5                                         152 CH.sub.3 CH.sub.3                                                                         H   CHC.sub.2 H.sub.5                                         153 C.sub.6 H.sub.5                                                                        CH.sub.3                                                                         H   CHC.sub.2 H.sub.5                                         154 C.sub.6 H.sub.5 CH.sub.2                                                               CH.sub.3                                                                         H   CHC.sub.2 H.sub.5                                         155 CH.sub.3 CO                                                                            CH.sub.3                                                                         H   CHC.sub.2 H.sub.5                                         156 C.sub.6 H.sub.5 CO                                                                     CH.sub.3                                                                         H   CHC.sub.2 H.sub.5                                         157 H        H  CH.sub.3                                                                          CHC.sub.2 H.sub.5                                         158 CH.sub.3 H  CH.sub.3                                                                          CHC.sub.2 H.sub.5                                         159 t-C.sub.4 H.sub.9                                                                      H  CH.sub.3                                                                          CHC.sub.2 H.sub.5                                         160 C.sub.6 H.sub.5                                                                        H  CH.sub.3                                                                          CHC.sub.2 H.sub.5                                         161 2-Cl-C.sub.6 H.sub.4                                                                   H  CH.sub.3                                                                          CHC.sub.2 H.sub.5                                         162 3-NO.sub.2C.sub.6 H.sub.4                                                              H  CH.sub.3                                                                          CHC.sub.2 H.sub.5                                         163 4-CH.sub.3 OC.sub.6 H.sub.4                                                            H  CH.sub.3                                                                          CHC.sub.2 H.sub.5                                         164 C.sub.6 H.sub.5 CH.sub.2                                                               H  CH.sub.3                                                                          CHC.sub.2 H.sub.5                                         165 2-ClC.sub.6 H.sub.4 CH.sub.2                                                           H  CH.sub.3                                                                          CHC.sub.2 H.sub.5                                         166 3-NO.sub.2 C.sub.6 H.sub.4 CH.sub.2                                                    H  CH.sub.3                                                                          CHC.sub.2 H.sub.5                                         167 4-CH.sub.3 OC.sub.6 H.sub.4 CH.sub.2                                                   H  CH.sub.3                                                                          CHC.sub.2 H.sub.5                                         168 CH.sub.3 CO                                                                            H  CH.sub.3                                                                          CHC.sub.2 H.sub.5                                         169 C.sub.6 H.sub.5 CO                                                                     H  CH.sub.3                                                                          CHC.sub.2 H.sub.5                                         170 CH.sub.3 CH.sub.3                                                                         CH.sub.3                                                                          CHC.sub.2 H.sub.5                                         171 C.sub.6 H.sub.5                                                                        CH.sub.3                                                                         CH.sub.3                                                                          CHC.sub.2 H.sub.5                                         172 C.sub.6 H.sub.5 CH.sub.2                                                               CH.sub.3                                                                         CH.sub.3                                                                          CHC.sub.2 H.sub.5                                         173 CH.sub.3 CO                                                                            CH.sub.3                                                                         CH.sub.3                                                                          CHC.sub.2 H.sub.5                                         174 C.sub.6 H.sub.5 CO                                                                     CH.sub.3                                                                         CH.sub.3                                                                          CHC.sub.2 H.sub.5                                         175 CH.sub.3 H  C.sub.6 H.sub.5                                                                   CHC.sub.2 H.sub.5                                         176 C.sub.6 H.sub.5                                                                        H  C.sub.6 H.sub.5                                                                   CHC.sub.2 H.sub.5                                         177 C.sub.6 H.sub.5 CH.sub.2                                                               H  C.sub.6 H.sub.5                                                                   CHC.sub.2 H.sub.5                                         178 CH.sub.3 CO                                                                            H  C.sub.6 H.sub.5                                                                   CHC.sub.2 H.sub.5                                         179 C.sub.6 H.sub.5 CO                                                                     H  C.sub.6 H.sub.5                                                                   CHC.sub.2 H.sub.5                                         180 CH.sub.3 CH.sub.3                                                                         C.sub.6 H.sub.5                                                                   CHC.sub.2 H.sub.5                                         181 C.sub.6 H.sub.5                                                                        CH.sub.3                                                                         C.sub.6 H.sub.5                                                                   CHC.sub.2 H.sub.5                                         182 C.sub.6 H.sub.5 CH.sub.2                                                               CH.sub.3                                                                         C.sub.6 H.sub.5                                                                   CHC.sub.2 H.sub.5                                         183 CH.sub.3 CO                                                                            CH.sub.3                                                                         C.sub.6 H.sub.5                                                                   CHC.sub.2 H.sub.5                                         184 C.sub.6 H.sub.5 CO                                                                     CH.sub.3                                                                         C.sub.6 H.sub.5                                                                   CHC.sub.2 H.sub.5                                         __________________________________________________________________________

                                      TABLE IX                                    __________________________________________________________________________     ##STR19##                                                                    No.  A             X      m.p. (°C.)                                                                   δ (C .sub.--H.sub.2C .sub.--H.sub.2)    __________________________________________________________________________    1    H             CHOCH.sub.3                                                2    CH.sub.3      CHOCH.sub.3                                                3    t-C.sub.4 H.sub.9                                                                           CHOCH.sub.3                                                4    C.sub.6 H.sub.5                                                                             CHOCH.sub.3                                                5    2-CH.sub.3 C.sub.6 H.sub.4                                                                  CHOCH.sub.3                                                6    2-ClC.sub.6 H.sub.4                                                                         CHOCH.sub.3                                                7    3-CH.sub.3 OC.sub.6 H.sub.4                                                                 CHOCH.sub.3                                                8    4-Cyano-C.sub.6 H.sub.4                                                                     CHOCH.sub.3                                                9    2,6-F.sub.2C.sub.6 H.sub.3                                                                  CHOCH.sub.3                                                10   β-Naphthyl                                                                             CHOCH.sub.3                                                11   3-Pyridyl     CHOCH.sub.3                                                12   2-Furyl       CHOCH.sub.3                                                13   N-Methyl-3-indolyl                                                                          CHOCH.sub.3                                                14   CF.sub.3      CHOCH.sub.3                                                15   HO            CHOCH.sub.3                                                16   t-C.sub.4 H.sub.9 O                                                                         CHOCH.sub.3                                                17   CH.sub.2CHCH.sub.2 O                                                                        CHOCH.sub.3                                                18   C.sub.6 H.sub.5 CH.sub.2 O                                                                  CHOCH.sub.3                                                19   2-CH.sub.3 C.sub.6 H.sub.4 CH.sub.2 O                                                       CHOCH.sub.3                                                20   2-ClC.sub.6 H.sub.4 CH.sub.2 O                                                              CHOCH.sub.3                                                21   3-CH.sub.3 OC.sub.6 H.sub.4 CH.sub.2 O                                                      CHOCH.sub.3                                                22   4-Cyano-C.sub.6 H.sub.4 CH.sub.2 O                                                          CHOCH.sub.3                                                23   2,6-F.sub.2C.sub.6 H.sub.3 CH.sub.2 O                                                       CHOCH.sub.3                                                24   2-Pyridyl-methoxy                                                                           CHOCH.sub.3                                                25   t-C.sub.4 H.sub.9(CH.sub.3).sub.2SiO                                                        CHOCH.sub.3                                                26   CH.sub.3 NH   CHOCH.sub.3                                                27   C.sub.6 H.sub.5 NH                                                                          CHOCH.sub.3                                                28   2-CH.sub.3 C.sub.6 H.sub.4 NH                                                               CHOCH.sub.3                                                29   2-ClC.sub.6 H.sub.4 NH                                                                      CHOCH.sub.3                                                30   3-CH.sub.3 OC.sub.6 H.sub.4 NH                                                              CHOCH.sub.3                                                31   4-Cyano-C.sub.6 H.sub.4 NH                                                                  CHOCH.sub.3                                                32   2,6-F.sub.2C.sub.6 H.sub.3 NH                                                               CHOCH.sub.3                                                33   C.sub.6 H.sub.5 NCH.sub.3                                                                   CHOCH.sub.3                                                34   2-ClC.sub.6 H.sub.4 NCH.sub.3                                                               CHOCH.sub.3                                                35   4-Cyano-C.sub.6 H.sub.4 NCH.sub.3                                                           CHOCH.sub.3                                                36   C.sub.6 H.sub.5 CH.sub.2 NH                                                                 CHOCH.sub.3                                                37   2-CH.sub.3 C.sub.6 H.sub.4 CH.sub.2 NH                                                      CHOCH.sub.3                                                38   2-ClC.sub.6 H.sub.4 CH.sub.2 NH                                                             CHOCH.sub.3                                                39   3-CH.sub.3 OC.sub.6 H.sub.4 CH.sub.2 NH                                                     CHOCH.sub.3                                                40   4-Cyano-C.sub.6 H.sub.4 CH.sub.2 NH                                                         CHOCH.sub.3                                                41   2,6-F.sub.2 C.sub.6 H.sub.3 CH.sub.2 NH                                                     CHOCH.sub.3                                                42   C.sub.6 H.sub.5 CH.sub.2 NCH.sub.3                                                          CHOCH.sub.3                                                43   2-ClC.sub.6 H.sub.4 CH.sub.2 NCH.sub.3                                                      CHOCH.sub.3                                                44   4-Cyano-C.sub.6 H.sub.4 CH.sub.2 NCH.sub.3                                                  CHOCH.sub.3                                                45   HS            CHOCH.sub.3                                                46   C.sub.6 H.sub.5 CH.sub.2 S                                                                  CHOCH.sub.3                                                47   H             NOCH.sub.3                                                 48   CH.sub.3      NOCH.sub.3                                                                           oil   2.69 (mc)                                     49   t-C.sub.4 H.sub.9                                                                           NOCH.sub.3                                                 50   C.sub.6 H.sub.5                                                                             NOCH.sub.3                                                                           oil                                                 51   2-CH.sub.3 C.sub.6 H.sub.4                                                                  NOCH.sub.3                                                 52   2-ClC.sub.6 H.sub.4                                                                         NOCH.sub.3                                                 53   3-CH.sub.3 OC.sub.6 H.sub.4                                                                 NOCH.sub.3                                                 54   4-Cyano-C.sub.6 H.sub.4                                                                     NOCH.sub.3                                                 55   2,6-F.sub.2C.sub.6 H.sub.3                                                                  NOCH.sub.3                                                 56   β-Naphthyl                                                                             NOCH.sub.3                                                 57   3-Pyridyl     NOCH.sub.3                                                 58   2-Furyl       NOCH.sub.3                                                 59   N-Methyl-3-indolyl                                                                          NOCH.sub.3                                                 60   CF.sub.3      NOCH.sub.3                                                 61   HO            NOCH.sub.3                                                 62   t-C.sub.4 H.sub.9 O                                                                         NOCH.sub.3                                                 63   CH.sub.2CHCH.sub.2 O                                                                        NOCH.sub.3                                                 64   C.sub.6 H.sub.5 CH.sub.2 O                                                                  NOCH.sub.3                                                 65   2-CH.sub.3 C.sub.6 H.sub.4 CH.sub.2 O                                                       NOCH.sub.3                                                 66   2-ClC.sub.6 H.sub. 4 CH.sub.2 O                                                             NOCH.sub.3                                                 67   3-CH.sub.3 OC.sub.6 H.sub.4 CH.sub.2 O                                                      NOCH.sub.3                                                 68   4-Cyano-C.sub.6 H.sub.4 CH.sub.2 O                                                          NOCH.sub.3                                                 69   2,6-F.sub.2C.sub.6 H.sub.3 CH.sub.2 O                                                       NOCH.sub.3                                                 70   2-Pyridyl-methoxy                                                                           NOCH.sub.3                                                 71   t-C.sub.4 H.sub.9(CH.sub.3).sub.2SiO                                                        NOCH.sub.3                                                 72   CH.sub.3 NH   NOCH.sub.3                                                 73   C.sub.6 H.sub.5 NH                                                                          NOCH.sub.3                                                 74   2-CH.sub.3 C.sub.6 H.sub.4 NH                                                               NOCH.sub.3                                                 75   2-ClC.sub.6 H.sub.4 NH                                                                      NOCH.sub.3                                                 76   3-CH.sub.3 OC.sub.6 H.sub.4 NH                                                              NOCH.sub.3                                                 77   4-Cyano-C.sub.6 H.sub.4 NH                                                                  NOCH.sub.3                                                 78   2,6-F.sub.2C.sub.6 H.sub.3 NH                                                               NOCH.sub.3                                                 79   C.sub.6 H.sub.5 NCH.sub.3                                                                   NOCH.sub.3                                                 80   2-ClC.sub.6 H.sub.4 NCH.sub.3                                                               NOCH.sub.3                                                 81   4-Cyano-C.sub.6 H.sub.4 NCH.sub.3                                                           NOCH.sub.3                                                 82   C.sub.6 H.sub.5 CH.sub.2 NH                                                                 NOCH.sub.3                                                 83   2-CH.sub.3 C.sub.6 H.sub.4 CH.sub.2 NH                                                      NOCH.sub.3                                                 84   2-ClC.sub.6 H.sub.4 CH.sub.2 NH                                                             NOCH.sub.3                                                 85   3-CH.sub.3 OC.sub.6 H.sub.4 CH.sub.2 NH                                                     NOCH.sub.3                                                 86   4-Cyano-C.sub.6 H.sub.4 CH.sub.2 NH                                                         NOCH.sub.3                                                 87   2,6-F.sub.2 C.sub.6 H.sub.3 CH.sub.2 NH                                                     NOCH.sub.3                                                 88   C.sub.6 H.sub.5 CH.sub.2 NCH.sub.3                                                          NOCH.sub.3                                                 89   2-ClC.sub.6 H.sub.4 CH.sub.2 NCH.sub.3                                                      NOCH.sub.3                                                 90   4-Cyano-C.sub.6 H.sub.4 CH.sub.2 NCH.sub.3                                                  NOCH.sub.3                                                 91   HS            NOCH.sub.3                                                 92   C.sub.6 H.sub.5 CH.sub.2 S                                                                  NOCH.sub.3                                                 93   H             CHCH.sub.3                                                 94   CH.sub.3      CHCH.sub.3                                                 95   t-C.sub.4 H.sub.9                                                                           CHCH.sub.3                                                 96   C.sub.6 H.sub.5                                                                             CHCH.sub.3                                                 97   2-CH.sub.3 C.sub.6 H.sub.4                                                                  CHCH.sub.3                                                 98   2-ClC.sub.6 H.sub.4                                                                         CHCH.sub.3                                                 99   3-CH.sub.3 OC.sub.6 H.sub.4                                                                 CHCH.sub.3                                                 100  4-Cyano-C.sub.6 H.sub.4                                                                     CHCH.sub.3                                                 101  2,6-F.sub.2C.sub.6 H.sub.3                                                                  CHCH.sub.3                                                 102  β-Naphthyl                                                                             CHCH.sub.3                                                 103  3-Pyridyl     CHCH.sub.3                                                 104  2-Furyl       CHCH.sub.3                                                 105  N-Methyl-3-indolyl                                                                          CHCH.sub.3                                                 106  CF.sub.3      CHCH.sub.3                                                 107  HO            CHCH.sub.3                                                 108  t-C.sub.4 H.sub.9 O                                                                         CHCH.sub.3                                                 109  CH.sub.2CHCH.sub.2 O                                                                        CHCH.sub.3                                                 110  C.sub.6 H.sub.5 CH.sub.2 O                                                                  CHCH.sub.3                                                 111  2-CH.sub.3 C.sub.6 H.sub.4 CH.sub.2 O                                                       CHCH.sub.3                                                 112  2-ClC.sub.6 H.sub.4 CH.sub.2 O                                                              CHCH.sub.3                                                 113  3-CH.sub. 3 OC.sub.6 H.sub.4 CH.sub.2 O                                                     CHCH.sub.3                                                 114  4-Cyano-C.sub.6 H.sub.4 CH.sub.2 O                                                          CHCH.sub.3                                                 115  2,6-F.sub.2C.sub.6 H.sub.3 CH.sub.2 O                                                       CHCH.sub.3                                                 116  2-Pyridyl-methoxy                                                                           CHCH.sub.3                                                 117  t-C.sub.4 H.sub.9(CH.sub.3).sub.2SiO                                                        CHCH.sub.3                                                 118  CH.sub.3 NH   CHCH.sub.3                                                 119  C.sub.6 H.sub.5 NH                                                                          CHCH.sub.3                                                 120  2-CH.sub.3 C.sub.6 H.sub.4 NH                                                               CHCH.sub.3                                                 121  2-ClC.sub.6 H.sub.4 NH                                                                      CHCH.sub.3                                                 122  3-CH.sub.3 OC.sub.6 H.sub.4 NH                                                              CHCH.sub.3                                                 123  4-Cyano-C.sub.6 H.sub.4 NH                                                                  CHCH.sub.3                                                 124  2,6-F.sub.2C.sub.6 H.sub.3 NH                                                               CHCH.sub.3                                                 125  C.sub.6 H.sub.5 NCH.sub.3                                                                   CHCH.sub.3                                                 126  2-ClC.sub.6 H.sub.4 NCH.sub.3                                                               CHCH.sub.3                                                 127  4-Cyano-C.sub.6 H.sub.4 NCH.sub.3                                                           CHCH.sub.3                                                 128  C.sub.6 H.sub.5 CH.sub.2 NH                                                                 CHCH.sub.3                                                 129  2-CH.sub.3 C.sub.6 H.sub.4 CH.sub.2 NH                                                      CHCH.sub.3                                                 130  2-ClC.sub.6 H.sub.4 CH.sub.2 NH                                                             CHCH.sub.3                                                 131  3-CH.sub.3 OC.sub.6 H.sub.4 CH.sub.2 NH                                                     CHCH.sub.3                                                 132  4-Cyano-C.sub.6 H.sub.4 CH.sub.2 NH                                                         CHCH.sub.3                                                 133  2,6-F.sub.2 C.sub.6 H.sub.3 CH.sub.2 NH                                                     CHCH.sub.3                                                 134  C.sub.6 H.sub.5 CH.sub.2 NCH.sub.3                                                          CHCH.sub.3                                                 135  2-ClC.sub.6 H.sub.4 CH.sub.2 NCH.sub.3                                                      CHCH.sub.3                                                 136  4-Cyano-C.sub.6 H.sub.4 CH.sub.2 NCH.sub.3                                                  CHCH.sub.3                                                 137  HS            CHCH.sub.3                                                 138  C.sub.6 H.sub.5 CH.sub.2 S                                                                  CHCH.sub.3                                                 139  H             CHC.sub.2 H.sub.5                                          140  CH.sub.3      CHC.sub.2 H.sub.5                                          141  t-C.sub.4 H.sub.9                                                                           CHC.sub.2 H.sub.5                                          142  C.sub.6 H.sub.5                                                                             CHC.sub.2 H.sub.5                                          143  2-CH.sub.3 C.sub.6 H.sub.4                                                                  CHC.sub.2 H.sub.5                                          144  2-ClC.sub.6 H.sub.4                                                                         CHC.sub.2 H.sub.5                                          145  3-CH.sub.3 OC.sub.6 H.sub.4                                                                 CHC.sub.2 H.sub.5                                          146  4-Cyano-C.sub.6 H.sub.4                                                                     CHC.sub.2 H.sub.5                                          147  2,6-F.sub.2C.sub.6 H.sub.3                                                                  CHC.sub.2 H.sub.5                                          148  β-Naphthyl                                                                             CHC.sub.2 H.sub.5                                          149  3-Pyridyl     CHC.sub.2 H.sub.5                                          150  2-Furyl       CHC.sub.2 H.sub.5                                          151  N-Methyl-3-indolyl                                                                          CHC.sub.2 H.sub.5                                          152  CF.sub.3      CHC.sub.2 H.sub.5                                          153  HO            CHC.sub.2 H.sub.5                                          154  t-C.sub.4 H.sub.9 O                                                                         CHC.sub.2 H.sub.5                                          155  CH.sub.2CHCH.sub.2 O                                                                        CHC.sub.2 H.sub.5                                          156  C.sub.6 H.sub.5 CH.sub.2 O                                                                  CHC.sub.2 H.sub.5                                          157  2-CH.sub.3 C.sub.6 H.sub.4 CH.sub.2 O                                                       CHC.sub.2 H.sub.5                                          158  2-ClC.sub.6 H.sub.4 CH.sub.2 O                                                              CHC.sub.2 H.sub.5                                          159  3-CH.sub.3 OC.sub.6 H.sub.4 CH.sub.2 O                                                      CHC.sub.2 H.sub.5                                          160  4-Cyano-C.sub.6 H.sub.4 CH.sub.2 O                                                          CHC.sub.2 H.sub.5                                          161  2,6-F.sub.2C.sub.6 H.sub.3 CH.sub.2 O                                                       CHC.sub.2 H.sub.5                                          162  2-Pyridyl-methoxy                                                                           CHC.sub.2 H.sub.5                                          163  t-C.sub.4 H.sub.9(CH.sub.3).sub.2SiO                                                        CHC.sub.2 H.sub.5                                          164  CH.sub.3 NH   CHC.sub.2 H.sub.5                                          165  C.sub.6 H.sub.5 NH                                                                          CHC.sub.2 H.sub.5                                          166  2-CH.sub.3 C.sub.6 H.sub.4 NH                                                               CHC.sub.2 H.sub.5                                          167  2-ClC.sub.6 H.sub.4 NH                                                                      CHC.sub.2 H.sub.5                                          168  3-CH.sub.3 OC.sub.6 H.sub.4 NH                                                              CHC.sub.2 H.sub.5                                          169  4-Cyano-C.sub.6 H.sub.4 NH                                                                  CHC.sub.2 H.sub.5                                          170  2,6-F.sub.2C.sub.6 H.sub.3 NH                                                               CHC.sub.2 H.sub.5                                          171  C.sub.6 H.sub.5 NCH.sub.3                                                                   CHC.sub.2 H.sub.5                                          172  2-ClC.sub.6 H.sub.4 NCH.sub.3                                                               CHC.sub.2 H.sub.5                                          173  4-Cyano-C.sub.6 H.sub.4 NCH.sub.3                                                           CHC.sub.2 H.sub.5                                          174  C.sub.6 H.sub.5 CH.sub.2 NH                                                                 CHC.sub.2 H.sub.5                                          175  2-CH.sub.3 C.sub.6 H.sub.4 CH.sub.2 NH                                                      CHC.sub.2 H.sub.5                                          176  2-ClC.sub.6 H.sub.4 CH.sub.2 NH                                                             CHC.sub.2 H.sub.5                                          177  3-CH.sub.3 OC.sub.6 H.sub.4 CH.sub.2 NH                                                     CHC.sub.2 H.sub.5                                          178  4-Cyano-C.sub.6 H.sub.4 CH.sub.2 NH                                                         CHC.sub.2 H.sub.5                                          179  2,6-F.sub.2 C.sub.6 H.sub.3 CH.sub.2 NH                                                     CHC.sub.2 H.sub.5                                          180  C.sub.6 H.sub.5 CH.sub.2 NCH.sub.3                                                          CHC.sub.2 H.sub.5                                          181  2-ClC.sub.6 H.sub.4 CH.sub.2 NCH.sub.3                                                      CHC.sub.2 H.sub.5                                          182  4-Cyano-C.sub.6 H.sub.4 CH.sub.2 NCH.sub.3                                                  CHC.sub.2 H.sub.5                                          183  HS            CHC.sub.2 H.sub.5                                          184  C.sub.6 H.sub.5 CH.sub.2 S                                                                  CHC.sub.2 H.sub.5                                          __________________________________________________________________________

                                      TABLE X                                     __________________________________________________________________________     ##STR20##                                                                                            Iso-                                                                             m.p.                                               No. A  B          X     mer                                                                              (°C.)                                                                     δ (C .sub.--H.sub.2 C .sub.--H.sub.2)     __________________________________________________________________________    1   H  CH.sub.3   CHOCH.sub.3                                                 2   H  t-C.sub.4 H.sub.9                                                                        CHOCH.sub.3                                                 3   H  C.sub.6 H.sub.5                                                                          CHOCH.sub.3                                                 4   H  2-CH.sub.3 C.sub.6 H.sub.4                                                               CHOCH.sub.3                                                 5   H  4-Cyano-C.sub.6 H.sub.4                                                                  CHOCH.sub.3                                                 6   H  2,6-F.sub.2 C.sub.6 H.sub.3                                                              CHOCH.sub.3                                                 7   CH.sub.3                                                                         CH.sub.3   CHOCH.sub.3                                                 8   CH.sub.3                                                                         t-C.sub.4 H.sub.9                                                                        CHOCH.sub.3                                                 9   CH.sub.3                                                                         C.sub.6 H.sub.5                                                                          CHOCH.sub.3                                                 10  CH.sub.3                                                                         2-CH.sub.3 C.sub.6 H.sub.4                                                               CHOCH.sub.3                                                 11  CH.sub.3                                                                         4-Cyano-C.sub.6 H.sub.4                                                                  CHOCH.sub.3                                                 12  CH.sub.3                                                                         2,6-F.sub.2 C.sub.6 H.sub.3                                                              CHOCH.sub.3                                                 13  C.sub.6 H.sub. 5                                                                 CH.sub.3   CHOCH.sub.3                                                 14  C.sub.6 H.sub.5                                                                  C.sub.6 H.sub.5                                                                          CHOCH.sub.3                                                 15  C.sub.6 H.sub.5                                                                  2,6-F.sub.2 C.sub.6 H.sub.3                                                              CHOCH.sub.3                                                 16  H  HO         CHOCH.sub.3                                                 17  H  CH.sub.3 O CHOCH.sub.3                                                 18  H  t-C.sub.4 H.sub.9 O                                                                      CHOCH.sub.3                                                 19  H  H.sub.2 CCClCH.sub.2 O                                                                   CHOCH.sub.3                                                 20  H  C.sub.6 H.sub.5 CH.sub.2 O                                                               CHOCH.sub.3                                                 21  H  2-CH.sub.3 C.sub.6 H.sub.4 CH.sub.2 O                                                    CHOCH.sub.3                                                 22  H  2-ClC.sub.6 H.sub.4 CH.sub.2 O                                                           CHOCH.sub.3                                                 23  H  3-CH.sub.3 OC.sub.6 H.sub.4 CH.sub.2 O                                                   CHOCH.sub.3                                                 24  H  4-Cyano-C.sub.6 H.sub.4 CH.sub.2 O                                                       CHOCH.sub.3                                                 25  H  2,6-F.sub.2 C.sub.6 H.sub.3 CH.sub.2 O                                                   CHOCH.sub.3                                                 26  H  3-Pyridylmethoxy                                                                         CHOCH.sub.3                                                 27  H  5-Chlorothien-2-ylme-                                                                    CHOCH.sub.3                                                        thoxy                                                                  28  H  CH.sub.3 CO                                                                              CHOCH.sub.3                                                 29  H  C.sub.6 H.sub.5 CO                                                                       CHOCH.sub.3                                                 30  CH.sub.3                                                                         HO         CHOCH.sub.3                                                 31  CH.sub.3                                                                         CH.sub.3 O CHOCH.sub.3                                                 32  CH.sub.3                                                                         t-C.sub.4 H.sub.9 O                                                                      CHOCH.sub.3                                                 33  CH.sub.3                                                                         H.sub.2 CCClCH.sub.2 O                                                                   CHOCH.sub.3                                                 34  CH.sub.3                                                                         C.sub. 6 H.sub.5 CH.sub.2 O                                                              CHOCH.sub.3                                                 35  CH.sub.3                                                                         2-CH.sub.3 C.sub.6 H.sub.4 CH.sub.2 O                                                    CHOCH.sub.3                                                 36  CH.sub.3                                                                         2-ClC.sub.6 H.sub.4 CH.sub.2 O                                                           CHOCH.sub.3                                                 37  CH.sub.3                                                                         3-CH.sub.3 OC.sub.6 H.sub.4 CH.sub.2 O                                                   CHOCH.sub.3                                                 38  CH.sub.3                                                                         4-Cyano-C.sub.6 H.sub.4 CH.sub.2 O                                                       CHOCH.sub.3                                                 39  CH.sub.3                                                                         2,6-F.sub.2 C.sub.6 H.sub.3 CH.sub.2 O                                                   CHOCH.sub.3                                                 40  CH.sub.3                                                                         3-Pyridylmethoxy                                                                         CHOCH.sub.3                                                 41  CH.sub.3                                                                         5-Chlorothien-2-ylme-                                                                    CHOCH.sub.3                                                        thoxy                                                                  42  CH.sub.3                                                                         CH.sub.3 CO                                                                              CHOCH.sub.3                                                 43  CH.sub.3                                                                         C.sub.6 H.sub.5 CO                                                                       CHOCH.sub.3                                                 44  C.sub.6 H.sub.5                                                                  HO         CHOCH.sub.3                                                 45  C.sub.6 H.sub.5                                                                  CH.sub.3 O CHOCH.sub.3                                                 46  C.sub.6 H.sub.5                                                                  H.sub.2 CCClCH.sub.2 O                                                                   CHOCH.sub.3                                                 47  C.sub.6 H.sub.5                                                                  C.sub.6 H.sub.5 CH.sub.2 O                                                               CHOCH.sub.3                                                 48  C.sub.6 H.sub.5                                                                  2,6-F.sub.2 C.sub.6 H.sub.3 CH.sub.2 O                                                   CHOCH.sub.3                                                 49  C.sub.6 H.sub.5                                                                  CH.sub.3 O CHOCH.sub.3                                                 50  H  CH.sub.3 NH                                                                              CHOCH.sub.3                                                 51  H  (CH.sub.3).sub.2 N                                                                       CHOCH.sub.3                                                 52  H  C.sub.6 H.sub.5 NH                                                                       CHOCH.sub.3                                                 53  H  2-ClC.sub.6 H.sub.4 NH                                                                   CHOCH.sub.3                                                 54  H  C.sub.6 H.sub.5 NCH.sub.3                                                                CHOCH.sub.3                                                 55  H  C.sub.6 H.sub.5 CH.sub.2 NH                                                              CHOCH.sub.3                                                 56  H  2-ClC.sub.6 H.sub.4 CH.sub.2 NH                                                          CHOCH.sub.3                                                 57  H  C.sub.6 H.sub.5 CH.sub.2 NCH.sub.3                                                       CHOCH.sub.3                                                 58  H  CH.sub.3 CO                                                                              CHOCH.sub.3                                                 59  H  C.sub.6 H.sub.5 CO                                                                       CHOCH.sub.3                                                 60  CH.sub.3                                                                         CH.sub.3 NH                                                                              CHOCH.sub.3                                                 61  CH.sub.3                                                                         (CH.sub.3).sub.2 N                                                                       CHOCH.sub.3                                                 62  CH.sub.3                                                                         C.sub.6 H.sub.5 NH                                                                       CHOCH.sub.3                                                 63  CH.sub.3                                                                         2-ClC.sub.6 H.sub.4 NH                                                                   CHOCH.sub.3                                                 64  CH.sub.3                                                                         C.sub.6 H.sub.5 NCH.sub.3                                                                CHOCH.sub.3                                                 65  CH.sub.3                                                                         C.sub.6 H.sub.5 CH.sub.2 NH                                                              CHOCH.sub.3                                                 66  CH.sub.3                                                                         2-ClC.sub.6 H.sub.4 CH.sub.2 NH                                                          CHOCH.sub.3                                                 67  CH.sub.3                                                                         C.sub.6 H.sub.5 CH.sub.2 NCH.sub.3                                                       CHOCH.sub.3                                                 68  CH.sub.3                                                                         CH.sub.3 CO                                                                              CHOCH.sub.3                                                 69  CH.sub.3                                                                         C.sub.6 H.sub.5 CO                                                                       CHOCH.sub.3                                                 70  C.sub.6 H.sub.5                                                                  CH.sub.3 NH                                                                              CHOCH.sub.3                                                 71  C.sub.6 H.sub.5                                                                  (CH.sub. 3).sub.2 N                                                                      CHOCH.sub.3                                                 72  C.sub.6 H.sub.5                                                                  C.sub.6 H.sub.5 NH                                                                       CHOCH.sub.3                                                 73  C.sub.6 H.sub.5                                                                  C.sub.6 H.sub.5 NCH.sub.3                                                                CHOCH.sub.3                                                 74  C.sub.6 H.sub.5                                                                  CH.sub.3 CO                                                                              CHOCH.sub.3                                                 75  C.sub.6 H.sub.5                                                                  C.sub.6 H.sub.5 CO                                                                       CHOCH.sub.3                                                 76  H  CH.sub.3   NOCH.sub.3                                                  77  H  t-C.sub.4 H.sub.9                                                                        NOCH.sub.3                                                  78  H  C.sub.6 H.sub.5                                                                          NOCH.sub.3                                                  79  H  2-CH.sub.3 C.sub.6 H.sub.4                                                               NOCH.sub.3                                                  80  H  4-Cyano-C.sub.6 H.sub.4                                                                  NOCH.sub.3                                                  81  H  2,6-F.sub.2 C.sub.6 H.sub.3                                                              NOCH.sub.3                                                  82  CH.sub.3                                                                         CH.sub.3   NOCH.sub.3                                                  83  CH.sub.3                                                                         t-C.sub.4 H.sub.9                                                                        NOCH.sub.3                                                  84  CH.sub.3                                                                         C.sub.6 H.sub.5                                                                          NOCH.sub.3                                                  85  CH.sub.3                                                                         2-CH.sub.3 C.sub.6 H.sub.4                                                               NOCH.sub.3                                                  86  CH.sub.3                                                                         4-Cyano-C.sub.6 H.sub.4                                                                  NOCH.sub.3                                                  87  CH.sub.3                                                                         2,6-F.sub.2 C.sub.6 H.sub.3                                                              NOCH.sub.3                                                  88  C.sub.6 H.sub.5                                                                  CH.sub.3   NOCH.sub.3                                                  89  C.sub.6 H.sub.5                                                                  C.sub.6 H.sub.5                                                                          NOCH.sub.3                                                  90  C.sub.6 H.sub.5                                                                  2,6-F.sub.2 C.sub.6 H.sub.3                                                              NOCH.sub.3                                                  91  H  HO         NOCH.sub.3                                                  92  H  CH.sub.3 O NOCH.sub.3                                                  93  H  t-C.sub.4 H.sub.9 O                                                                      NOCH.sub.3                                                  94  H  H.sub.2 CCClCH.sub.2 O                                                                   NOCH.sub.3                                                  95  H  C.sub.6 H.sub.5 CH.sub.2 O                                                               NOCH.sub.3                                                  96  H  2-CH.sub.3 C.sub.6 H.sub.4 CH.sub.2 O                                                    NOCH.sub.3                                                  97  H  2-ClC.sub.6 H.sub.4 CH.sub.2 O                                                           NOCH.sub.3                                                  98  H  3-CH.sub.3 OC.sub.6 H.sub.4 CH.sub.2 O                                                   NOCH.sub.3                                                  99  H  4-Cyano-C.sub.6 H.sub.4 CH.sub.2 O                                                       NOCH.sub.3                                                  100 H  2,6-F.sub.2 C.sub.6 H.sub.3 CH.sub.2 O                                                   NOCH.sub.3                                                  101 H  3-Pyridylmethoxy                                                                         NOCH.sub.3                                                  102 H  5-Chlorothien-2-ylme-                                                                    NOCH.sub.3                                                         thoxy                                                                  103 H  CH.sub.3 CO                                                                              NOCH.sub.3                                                  104 H  C.sub.6 H.sub.5 CO                                                                       NOCH.sub.3                                                  105 CH.sub.3                                                                         HO         NOCH.sub.3                                                  106 CH.sub.3                                                                         CH.sub.3 O NOCH.sub.3                                                  107 CH.sub.3                                                                         t-C.sub.4 H.sub.9 O                                                                      NOCH.sub.3                                                  108 CH.sub.3                                                                         H.sub.2 CCClCH.sub.2 O                                                                   NOCH.sub.3                                                  109 CH.sub.3                                                                         C.sub.6 H.sub.5 CH.sub.2 O                                                               NOCH.sub.3                                                  110 CH.sub.3                                                                         2-CH.sub.3 C.sub.6 H.sub.4 CH.sub.2 O                                                    NOCH.sub.3                                                  111 CH.sub.3                                                                         2-ClC.sub.6 H.sub.4 CH.sub.2 O                                                           NOCH.sub.3                                                  112 CH.sub.3                                                                         3-CH.sub.3 OC.sub.6 H.sub.4 CH.sub.2 O                                                   NOCH.sub.3                                                  113 CH.sub.3                                                                         4-Cyano-C.sub.6 H.sub.4 CH.sub.2 O                                                       NOCH.sub.3                                                  114 CH.sub.3                                                                         2,6-F.sub.2 C.sub.6 H.sub.3 CH.sub.2 O                                                   NOCH.sub.3                                                  115 CH.sub.3                                                                         3-Pyridylmethoxy                                                                         NOCH.sub.3                                                  116 CH.sub.3                                                                         5-Chlorothien-2-ylme-                                                                    NOCH.sub.3                                                         thoxy                                                                  117 CH.sub.3                                                                         CH.sub.3 CO                                                                              NOCH.sub.3                                                  118 CH.sub.3                                                                         C.sub.6 H.sub.5 CO                                                                       NOCH.sub.3                                                  119 C.sub.6 H.sub.5                                                                  HO         NOCH.sub.3                                                  120 C.sub.6 H.sub.5                                                                  CH.sub.3 O NOCH.sub.3                                                  121 C.sub.6 H.sub.5                                                                  H.sub.2 CCClCH.sub.2 O                                                                   NOCH.sub.3                                                  122 C.sub.6 H.sub.5                                                                  C.sub.6 H.sub.5 CH.sub.2 O                                                               NOCH.sub.3                                                  123 C.sub.6 H.sub.5                                                                  2,6-F.sub.2 C.sub.6 H.sub.3 CH.sub.2 O                                                   NOCH.sub.3                                                  124 C.sub.6 H.sub.5                                                                  CH.sub.3 O NOCH.sub.3                                                  125 H  CH.sub.3 NH                                                                              NOCH.sub.3                                                  126 H  (CH.sub.3).sub.2 N                                                                       NOCH.sub.3                                                  127 H  C.sub.6 H.sub.5 NH                                                                       NOCH.sub.3                                                  128 H  2-ClC.sub.6 H.sub.4 NH                                                                   NOCH.sub.3                                                  129 H  C.sub.6 H.sub.5 NCH.sub.3                                                                NOCH.sub.3                                                  130 H  C.sub.6 H.sub.5 CH.sub.2 NH                                                              NOCH.sub.3                                                  131 H  2-ClC.sub.6 H.sub.4 CH.sub.2 NH                                                          NOCH.sub.3                                                  132 H  C.sub.6 H.sub.5 CH.sub.2 NCH.sub.3                                                       NOCH.sub.3                                                  133 H  CH.sub.3 CO                                                                              NOCH.sub.3                                                  134 H  C.sub.6 H.sub.5 CO                                                                       NOCH.sub.3                                                  135 CH.sub.3                                                                         CH.sub.3 NH                                                                              NOCH.sub.3                                                  136 CH.sub.3                                                                         (CH.sub.3).sub.2 N                                                                       NOCH.sub.3                                                  137 CH.sub.3                                                                         C.sub.6 H.sub.5 NH                                                                       NOCH.sub.3                                                  138 CH.sub.3                                                                         2-ClC.sub.6 H.sub.4 NH                                                                   NOCH.sub.3                                                  139 CH.sub.3                                                                         C.sub.6 H.sub.5 NCH.sub.3                                                                NOCH.sub.3                                                  140 CH.sub.3                                                                         C.sub.6 H.sub.5 CH.sub.2 NH                                                              NOCH.sub.3                                                  141 CH.sub.3                                                                         2-ClC.sub.6 H.sub.4 CH.sub.2 NH                                                          NOCH.sub.3                                                  142 CH.sub.3                                                                         C.sub.6 H.sub.5 CH.sub.2 NCH.sub.3                                                       NOCH.sub.3                                                  143 CH.sub.3                                                                         CH.sub.3 CO                                                                              NOCH.sub.3                                                  144 CH.sub.3                                                                         C.sub.6 H.sub.5 CO                                                                       NOCH.sub.3                                                  145 C.sub.6 H.sub.5                                                                  CH.sub.3 NH                                                                              NOCH.sub.3                                                  146 C.sub.6 H.sub.5                                                                  (CH.sub.3).sub.2 N                                                                       NOCH.sub.3                                                  147 C.sub.6 H.sub.5                                                                  C.sub.6 H.sub.5 NH                                                                       NOCH.sub.3                                                  148 C.sub.6 H.sub.5                                                                  C.sub.6 H.sub.5 NCH.sub.3                                                                NOCH.sub.3                                                  149 C.sub.6 H.sub.5                                                                  CH.sub.3 CO                                                                              NOCH.sub.3                                                  150 C.sub.6 H.sub.5                                                                  C.sub.6 H.sub.5 CO                                                                       NOCH.sub.3                                                  151 H  CH.sub.3   CHCH.sub.3                                                  152 H  t-C.sub.4 H.sub.9                                                                        CHCH.sub.3                                                  153 H  C.sub.6 H.sub.5                                                                          CHCH.sub.3                                                  154 H  2-CH.sub.3 C.sub.6 H.sub.4                                                               CHCH.sub.3                                                  155 H  4-Cyano-C.sub.6 H.sub.4                                                                  CHCH.sub.3                                                  156 H  2,6-F.sub.2 C.sub.6 H.sub.3                                                              CHCH.sub.3                                                  157 CH.sub.3                                                                         CH.sub.3   CHCH.sub.3                                                  158 CH.sub.3                                                                         t-C.sub.4 H.sub.9                                                                        CHCH.sub.3                                                  159 CH.sub.3                                                                         C.sub.6 H.sub.5                                                                          CHCH.sub.3                                                  160 CH.sub.3                                                                         2-CH.sub.3 C.sub.6 H.sub.4                                                               CHCH.sub.3                                                  161 CH.sub.3                                                                         4-Cyano-C.sub.6 H.sub.4                                                                  CHCH.sub.3                                                  162 CH.sub.3                                                                         2,6-F.sub.2 C.sub.6 H.sub.3                                                              CHCH.sub.3                                                  163 C.sub.6 H.sub.5                                                                  CH.sub.3   CHCH.sub.3                                                  164 C.sub.6 H.sub.5                                                                  C.sub.6 H.sub.5                                                                          CHCH.sub.3                                                  165 C.sub.6 H.sub.5                                                                  2,6-F.sub.2 C.sub.6 H.sub.3                                                              CHCH.sub.3                                                  166 H  HO         CHCH.sub.3                                                  167 H  CH.sub.3 O CHCH.sub.3                                                  168 H  t-C.sub.4 H.sub.9 O                                                                      CHCH.sub.3                                                  169 H  H.sub.2 CCClCH.sub.2 O                                                                   CHCH.sub.3                                                  170 H  C.sub.6 H.sub.5 CH.sub.2 O                                                               CHCH.sub.3                                                  171 H  2-CH.sub.3 C.sub.6 H.sub.4 CH.sub.2 O                                                    CHCH.sub.3                                                  172 H  2-ClC.sub.6 H.sub.4 CH.sub.2 O                                                           CHCH.sub.3                                                  173 H  3-CH.sub.3 OC.sub.6 H.sub.4 CH.sub.2 O                                                   CHCH.sub.3                                                  174 H  4-Cyano-C.sub.6 H.sub.4 CH.sub.2 O                                                       CHCH.sub.3                                                  175 H  2,6-F.sub.2 C.sub.6 H.sub.3 CH.sub.2 O                                                   CHCH.sub.3                                                  176 H  3-Pyridylmethoxy                                                                         CHCH.sub.3                                                  177 H  5-Chlorothien-2-ylme-                                                                    CHCH.sub.3                                                         thoxy                                                                  178 H  CH.sub.3 CO                                                                              CHCH.sub.3                                                  179 H  C.sub.6 H.sub.5 CO                                                                       CHCH.sub.3                                                  180 CH.sub.3                                                                         HO         CHCH.sub.3                                                  181 CH.sub.3                                                                         CH.sub.3 O CHCH.sub.3                                                  182 CH.sub.3                                                                         t-C.sub.4 H.sub.9 O                                                                      CHCH.sub.3                                                  183 CH.sub.3                                                                         H.sub.2 CCClCH.sub.2 O                                                                   CHCH.sub.3                                                  184 CH.sub.3                                                                         C.sub.6 H.sub.5 CH.sub.2 O                                                               CHCH.sub.3                                                  185 CH.sub.3                                                                         2-CH.sub.3 C.sub.6 H.sub.4 CH.sub.2 O                                                    CHCH.sub.3                                                  186 CH.sub.3                                                                         2-ClC.sub.6 H.sub.4 CH.sub.2 O                                                           CHCH.sub.3                                                  187 CH.sub.3                                                                         3-CH.sub.3 OC.sub.6 H.sub.4 CH.sub.2 O                                                   CHCH.sub.3                                                  188 CH.sub.3                                                                         4-Cyano-C.sub.6 H.sub.4 CH.sub.2 O                                                       CHCH.sub.3                                                  189 CH.sub.3                                                                         2,6-F.sub.2 C.sub.6 H.sub.4 CH.sub.2 O                                                   CHCH.sub.3                                                  190 CH.sub.3                                                                         3-Pyridylmethoxy                                                                         CHCH.sub.3                                                  191 CH.sub.3                                                                         5-Chlorothien-2-ylme-                                                                    CHCH.sub.3                                                         thoxy                                                                  192 CH.sub.3                                                                         CH.sub.3 CO                                                                              CHCH.sub.3                                                  193 CH.sub.3                                                                         C.sub.6 H.sub.5 CO                                                                       CHCH.sub.3                                                  194 C.sub.6 H.sub.5                                                                  HO         CHCH.sub.3                                                  195 C.sub.6 H.sub.5                                                                  CH.sub.3 O CHCH.sub.3                                                  196 C.sub.6 H.sub.5                                                                  H.sub.2 CCClCH.sub.2 O                                                                   CHCH.sub.3                                                  197 C.sub.6 H.sub.5                                                                  C.sub.6 H.sub.5 CH.sub.2 O                                                               CHCH.sub.3                                                  198 C.sub.6 H.sub.5                                                                  2,6-F.sub.2 C.sub.6 H.sub.3 CH.sub.2 O                                                   CHCH.sub.3                                                  199 C.sub.6 H.sub.5                                                                  CH.sub.3 O CHCH.sub.3                                                  200 H  CH.sub.3 NH                                                                              CHCH.sub.3                                                  201 H  (CH.sub.3).sub.2 N                                                                       CHCH.sub.3                                                  202 H  C.sub.6 H.sub.5 NH                                                                       CHCH.sub.3                                                  203 H  2-ClC.sub.6 H.sub.4 NH                                                                   CHCH.sub.3                                                  204 H  C.sub.6 H.sub.5 NCH.sub.3                                                                CHCH.sub.3                                                  205 H  C.sub.6 H.sub.5 CH.sub.2 NH                                                              CHCH.sub.3                                                  206 H  2-ClC.sub.6 H.sub.4 CH.sub.2 NH                                                          CHCH.sub.3                                                  207 H  C.sub.6 H.sub.5 CH.sub.2 NCH.sub.3                                                       CHCH.sub.3                                                  208 H  CH.sub.3 CO                                                                              CHCH.sub.3                                                  209 H  C.sub.6 H.sub.5 CO                                                                       CHCH.sub.3                                                  210 CH.sub.3                                                                         CH.sub.3 NH                                                                              CHCH.sub.3                                                  211 CH.sub.3                                                                         (CH.sub.3).sub.2 N                                                                       CHCH.sub.3                                                  212 CH.sub.3                                                                         C.sub.6 H.sub.5 NH                                                                       CHCH.sub.3                                                  213 CH.sub.3                                                                         2-ClC.sub.6 H.sub.4 NH                                                                   CHCH.sub.3                                                  214 CH.sub.3                                                                         C.sub.6 H.sub.5 NCH.sub.3                                                                CHCH.sub.3                                                  215 CH.sub.3                                                                         C.sub.6 H.sub.5 CH.sub.2 NH                                                              CHCH.sub.3                                                  216 CH.sub.3                                                                         2-ClC.sub.6 H.sub.4 CH.sub.2 NH                                                          CHCH.sub.3                                                  217 CH.sub.3                                                                         C.sub.6 H.sub.5 CH.sub.2 NCH.sub.3                                                       CHCH.sub.3                                                  218 CH.sub.3                                                                         CH.sub.3 CO                                                                              CHCH.sub.3                                                  219 CH.sub.3                                                                         C.sub.6 H.sub.5 CO                                                                       CHCH.sub.3                                                  220 C.sub.6 H.sub.5                                                                  CH.sub.3 NH                                                                              CHCH.sub.3                                                  221 C.sub.6 H.sub.5                                                                  (CH.sub.3).sub.2 N                                                                       CHCH.sub.3                                                  222 C.sub.6 H.sub.5                                                                  C.sub.6 H.sub.5 NH                                                                       CHCH.sub.3                                                  223 C.sub.6 H.sub.5                                                                  C.sub.6 H.sub.5 NCH.sub.3                                                                CHCH.sub.3                                                  224 C.sub.6 H.sub.5                                                                  CH.sub.3 CO                                                                              CHCH.sub.3                                                  225 C.sub.6 H.sub.5                                                                  C.sub.6 H.sub.5 CO                                                                       CHCH.sub.3                                                  226 H  CH.sub.3   CHC.sub.2 H.sub.5                                           227 H  t-C.sub.4 H.sub.9                                                                        CHC.sub.2 H.sub.5                                           228 H  C.sub.6 H.sub.5                                                                          CHC.sub.2 H.sub.5                                           229 H  2-CH.sub.3 C.sub.6 H.sub.4                                                               CHC.sub.2 H.sub.5                                           230 H  4-Cyano-C.sub.6 H.sub.4                                                                  CHC.sub.2 H.sub.5                                           231 H  2,6-F.sub.2 C.sub.6 H.sub.3                                                              CHC.sub.2 H.sub.5                                           232 CH.sub.3                                                                         CH.sub.3   CHC.sub.2 H.sub.5                                           233 CH.sub.3                                                                         t-C.sub.4 H.sub.9                                                                        CHC.sub.2 H.sub.5                                           234 CH.sub.3                                                                         C.sub.6 H.sub.5                                                                          CHC.sub.2 H.sub.5                                           235 CH.sub.3                                                                         2-CH.sub.3 C.sub.6 H.sub.4                                                               CHC.sub.2 H.sub.5                                           236 CH.sub.3                                                                         4-Cyano-C.sub.6 H.sub.4                                                                  CHC.sub.2 H.sub.5                                           237 CH.sub.3                                                                         2,6-F.sub.2 C.sub.6 H.sub.3                                                              CHC.sub.2 H.sub.5                                           238 C.sub.6 H.sub.5                                                                  CH.sub.3   CHC.sub.2 H.sub.5                                           239 C.sub.6 H.sub.5                                                                  C.sub.6 H.sub.5                                                                          CHC.sub.2 H.sub.5                                           240 C.sub.6 H.sub.5                                                                  2,6-F.sub.2 C.sub.6 H.sub.3                                                              CHC.sub.2 H.sub.5                                           241 H  HO         CHC.sub.2 H.sub.5                                           242 H  CH.sub.3 O CHC.sub.2 H.sub.5                                           243 H  t-C.sub.4 H.sub.9 O                                                                      CHC.sub.2 H.sub.5                                           244 H  H.sub.2 CCClCH.sub.2 O                                                                   CHC.sub.2 H.sub.5                                           245 H  C.sub.6 H.sub.5 CH.sub.2 O                                                               CHC.sub. 2 H.sub.5                                          246 H  2-CH.sub.3 C.sub.6 H.sub.4 CH.sub.2 O                                                    CHC.sub.2 H.sub.5                                           247 H  2-ClC.sub.6 H.sub.4 CH.sub.2 O                                                           CHC.sub.2 H.sub.5                                           248 H  3-CH.sub.3 OC.sub.6 H.sub.4 CH.sub.2 O                                                   CHC.sub.2 H.sub.5                                           249 H  4-Cyano-C.sub.6 H.sub.4 CH.sub.2 O                                                       CHC.sub.2 H.sub.5                                           250 H  2,6-F.sub.2 C.sub.6 H.sub.3 CH.sub.2 O                                                   CHC.sub.2 H.sub.5                                           251 H  3-Pyridylmethoxy                                                                         CHC.sub.2 H.sub.5                                           252 H  5-Chlorothien-2-ylme-                                                                    CHC.sub.2 H.sub.5                                                  thoxy                                                                  253 H  CH.sub.3 CO                                                                              CHC.sub.2 H.sub.5                                           254 H  C.sub.6 H.sub.5 CO                                                                       CHC.sub.2 H.sub.5                                           255 CH.sub.3                                                                         HO         CHC.sub.2 H.sub.5                                           256 CH.sub.3                                                                         CH.sub.3 O CHC.sub.2 H.sub.5                                           257 CH.sub.3                                                                         t-C.sub.4 H.sub.9 O                                                                      CHC.sub.2 H.sub.5                                           258 CH.sub.3                                                                         H.sub.2 CCClCH.sub.2 O                                                                   CHC.sub.2 H.sub.5                                           259 CH.sub.3                                                                         C.sub.6 H.sub.5 CH.sub.2 O                                                               CHC.sub.2 H.sub.5                                           260 CH.sub.3                                                                         2-CH.sub.3 C.sub.6 H.sub.4 CH.sub.2 O                                                    CHC.sub.2 H.sub.5                                           261 CH.sub.3                                                                         2-ClC.sub.6 H.sub.4 CH.sub.2 O                                                           CHC.sub.2 H.sub.5                                           262 CH.sub.3                                                                         3-CH.sub.3 OC.sub.6 H.sub.4 CH.sub.2 O                                                   CHC.sub.2 H.sub.5                                           263 CH.sub.3                                                                         4-Cyano-C.sub.6 H.sub.4 CH.sub.2 O                                                       CHC.sub.2 H.sub.5                                           264 CH.sub.3                                                                         2,6-F.sub.2 C.sub.6 H.sub.3 CH.sub.2 O                                                   CHC.sub.2 H.sub.5                                           265 CH.sub.3                                                                         3-Pyridylmethoxy                                                                         CHC.sub.2 H.sub.5                                           266 CH.sub.3                                                                         5-Chlorothien-2-ylme-                                                                    CHC.sub.2 H.sub.5                                                  thoxy                                                                  267 CH.sub.3                                                                         CH.sub.3 CO                                                                              CHC.sub.2 H.sub.5                                           268 CH.sub.3                                                                         C.sub.6 H.sub.5 CO                                                                       CHC.sub.2 H.sub.5                                           269 C.sub.6 H.sub.5                                                                  HO         CHC.sub.2 H.sub.5                                           270 C.sub.6 H.sub.5                                                                  CH.sub.3 O CHC.sub.2 H.sub.5                                           271 C.sub.6 H.sub.5                                                                  H.sub.2 CCClCH.sub.2 O                                                                   CHC.sub.2 H.sub.5                                           272 C.sub.6 H.sub.5                                                                  C.sub.6 H.sub.5 CH.sub.2 O                                                               CHC.sub.2 H.sub.5                                           273 C.sub.6 H.sub.5                                                                  2,6-F.sub.2 C.sub.6 H.sub.3 CH.sub.2 O                                                   CHC.sub.2 H.sub.5                                           274 C.sub.6 H.sub.5                                                                  CH.sub.3 O CHC.sub.2 H.sub.5                                           275 H  CH.sub.3 NH                                                                              CHC.sub.2 H.sub.5                                           276 H  (CH.sub.3).sub.2 N                                                                       CHC.sub.2 H.sub.5                                           277 H  C.sub.6 H.sub.5 NH                                                                       CHC.sub.2 H.sub.5                                           278 H  2-ClC.sub.6 H.sub.4 NH                                                                   CHC.sub.2 H.sub.5                                           279 H  C.sub.6 H.sub.5 NCH.sub.3                                                                CHC.sub.2 H.sub.5                                           280 H  C.sub.6 H.sub.5 CH.sub.2 NH                                                              CHC.sub.2 H.sub.5                                           281 H  2-ClC.sub.6 H.sub.4 CH.sub.2 NH                                                          CHC.sub.2 H.sub.5                                           282 H  C.sub.6 H.sub.5 CH.sub.2 NCH.sub.3                                                       CHC.sub.2 H.sub.5                                           283 H  CH.sub.3 CO                                                                              CHC.sub.2 H.sub.5                                           284 H  C.sub.6 H.sub.5 CO                                                                       CHC.sub.2 H.sub.5                                           285 CH.sub.3                                                                         CH.sub.3 NH                                                                              CHC.sub.2 H.sub.5                                           286 CH.sub.3                                                                         (CH.sub.3).sub.2 N                                                                       CHC.sub.2 H.sub.5                                           287 CH.sub.3                                                                         C.sub.6 H.sub.5 NH                                                                       CHC.sub.2 H.sub.5                                           288 CH.sub.3                                                                         2-ClC.sub.6 H.sub.4 NH                                                                   CHC.sub.2 H.sub.5                                           289 CH.sub.3                                                                         C.sub.6 H.sub.5 NCH.sub.3                                                                CHC.sub.2 H.sub.5                                           290 CH.sub.3                                                                         C.sub.6 H.sub.5 CH.sub.2 NH                                                              CHC.sub.2 H.sub.5                                           291 CH.sub.3                                                                         2-ClC.sub.6 H.sub.4 CH.sub.2 NH                                                          CHC.sub.2 H.sub.5                                           292 CH.sub.3                                                                         C.sub.6 H.sub.5 CH.sub.2 NCH.sub.3                                                       CHC.sub.2 H.sub.5                                           293 CH.sub.3                                                                         CH.sub.3 CO                                                                              CHC.sub.2 H.sub.5                                           294 CH.sub.3                                                                         C.sub.6 H.sub.5 CO                                                                       CHC.sub.2 H.sub.5                                           295 C.sub.6 H.sub.5                                                                  CH.sub.3 NH                                                                              CHC.sub.2 H.sub.5                                           296 C.sub.6 H.sub.5                                                                  (CH.sub.3).sub.2 N                                                                       CHC.sub.2 H.sub.5                                           297 C.sub.6 H.sub.5                                                                  C.sub.6 H.sub.5 NH                                                                       CHC.sub.2 H.sub.5                                           298 C.sub.6 H.sub.5                                                                  C.sub.6 H.sub.5 NCH.sub.3                                                                CHC.sub.2 H.sub.5                                           299 C.sub.6 H.sub.5                                                                  CH.sub.3 CO                                                                              CHC.sub.2 H.sub.5                                           300 C.sub.6 H.sub.5                                                                  C.sub.6 H.sub.5 CO                                                                       CHC.sub.2 H.sub.5                                           __________________________________________________________________________

                                      TABLE XI                                    __________________________________________________________________________     ##STR21##                                                                                            Iso-                                                                             m.p.                                               No. R            X      mer                                                                              (°C.)                                                                        δ(CC .sub.--H)                         __________________________________________________________________________    1   H            CHOCH.sub.3                                                  2   CH.sub.3     CHOCH.sub.3                                                  3   C.sub.2 H.sub.5                                                                            CHOCH.sub.3                                                  4   i-C.sub.3 H.sub.7                                                                          CHOCH.sub.3                                                  5   t-C.sub.4 H.sub.9                                                                          CHOCH.sub.3                                                                          a  oil   6.65                                         6   Allyl        CHOCH.sub.3                                                  7   2-Chloroallyl                                                                              CHOCH.sub.3                                                  8   2-Methylallyl                                                                              CHOCH.sub.3                                                  9   Benzyl       CHOCH.sub.3                                                  10  2-Methoxybenzyl                                                                            CHOCH.sub.3                                                  11  3-Trifluoromethylbenzyl                                                                    CHOCH.sub.3                                                  12  4-Methylbenzyl                                                                             CHOCH.sub.3                                                  13  3,5-Dichlorobenzyl                                                                         CHOCH.sub.3                                                  14  (2-Pyridyl)-methyl                                                                         CHOCH.sub.3                                                  15  5-Chlorothien-2-ylmethyl                                                                   CHOCH.sub.3                                                  16  H            NOCH.sub.3                                                   17  CH.sub.3     NOCH.sub.3                                                   18  C.sub.2 H.sub.5                                                                            NOCH.sub.3                                                   19  i-C.sub.3 H.sub.7                                                                          NOCH.sub.3                                                   20  t-C.sub.4 H.sub.9                                                                          NOCH.sub.3                                                                           a  oil   6.62                                         21  Allyl        NOCH.sub.3                                                   22  2-Chloroallyl                                                                              NOCH.sub.3                                                   23  2-Methylallyl                                                                              NOCH.sub.3                                                   24  Benzyl       NOCH.sub.3                                                   25  2-Methoxybenzyl                                                                            NOCH.sub.3                                                   26  3-Trifluoromethylbenzyl                                                                    NOCH.sub.3                                                                           a  oil   6.72                                         27  4-Methylbenzyl                                                                             NOCH.sub.3                                                   28  3,5-Dichlorobenzyl                                                                         NOCH.sub.3                                                   29  (2-Pyridyl)-methyl                                                                         NOCH.sub.3                                                   30  5-Chlorothien-2-ylmethyl                                                                   NOCH.sub.3                                                   31  H            CHCH.sub.3                                                   32  CH.sub.3     CHCH.sub.3                                                   33  C.sub.2 H.sub.5                                                                            CHCH.sub.3                                                   34  i-C.sub.3 H.sub.7                                                                          CHCH.sub.3                                                   35  t-C.sub.4 H.sub.9                                                                          CHCH.sub.3                                                   36  Allyl        CHCH.sub.3                                                   37  2-Chloroallyl                                                                              CHCH.sub.3                                                   38  2-Methylallyl                                                                              CHCH.sub.3                                                   39  Benzyl       CHCH.sub.3                                                   40  2-Methoxybenzyl                                                                            CHCH.sub.3                                                   41  3-Trifluoromethylbenzyl                                                                    CHCH.sub.3                                                   42  4-Methylbenzyl                                                                             CHCH.sub.3                                                   43  3,5-Dichlorobenzyl                                                                         CHCH.sub.3                                                   44  (2-Pyridyl)-methyl                                                                         CHCH.sub.3                                                   45  5-Chlorothien-2-ylmethyl                                                                   CHCH.sub.3                                                   46  H            CHC.sub.2 H.sub.5                                            47  CH.sub.3     CHC.sub.2 H.sub.5                                            48  C.sub.2 H.sub.5                                                                            CHC.sub.2 H.sub.5                                            49  i-C.sub.3 H.sub.7                                                                          CHC.sub.2 H.sub.5                                            50  t-C.sub.4 H.sub.9                                                                          CHC.sub.2 H.sub.5                                            51  Allyl        CHC.sub.2 H.sub.5                                            52  2-Chloroallyl                                                                              CHC.sub.2 H.sub.5                                            53  2-Methylallyl                                                                              CHC.sub.2 H.sub.5                                            54  Benzyl       CHC.sub.2 H.sub.5                                            55  2-Methoxybenzyl                                                                            CHC.sub.2 H.sub.5                                            56  3-Trifluoromethylbenzyl                                                                    CHC.sub.2 H.sub.5                                            57  4-Methylbenzyl                                                                             CHC.sub.2 H.sub.5                                            58  3,5-Dichlorobenzyl                                                                         CHC.sub.2 H.sub.5                                            59  (2-Pyridyl)-methyl                                                                         CHC.sub.2 H.sub.5                                            60  5-Chlorothien-2-ylmethyl                                                                   CHC.sub.2 H.sub.5                                            __________________________________________________________________________

The novel compounds are suitable as fungicides.

The fungicidal compounds I, or agents containing them, may be appliedfor instance in the form of directly sprayable solutions, powders,suspensions (including high-percentage aqueous, oily or othersuspensions), dispersions, emulsions, oil dispersions, pastes, dusts,broadcasting agents, or granules by spraying, atomizing, dusting,broadcasting or watering. The forms of application depend entirely onthe purpose for which the agents are being used, but they must ensure asfine a distribution of the active ingredients according to the inventionas possible.

Normally, the plants are sprayed or dusted with the active ingredients,or the seeds of the plants are treated with the active ingredients.

The formulations are produced in known manner, for example by extendingthe active ingredient with solvents and/or carriers, with or without theuse of emulsifiers and dispersants; if water is used as solvent, it isalso possible to employ other organic solvents as auxiliary solvents.Suitable auxiliaries for this purpose are solvents such as aromatics(e.g., xylene), chlorinated aromatics (e.g., chlorobenzenes), paraffins(e.g., crude oil fractions), alcohols (e.g., methanol, butanol), ketones(e.g., cyclohexanone), amines (e.g., ethanolamine, dimethylformamide),and water; carriers such as ground natural minerals (e.g., kaolins,aluminas, talc and chalk) and ground synthetic minerals (e.g., highlydisperse silica and silicates); emulsifiers such as nonionic and anionicemulsifiers (e.g., polyoxyethylene fatty alcohol ethers, alkylsulfonates and aryl sulfonates); and dispersants such as lignin-sulfitewaste liquors and methylcellulose.

Examples of surfactants are: alkali metal, alkaline earth metal andammonium salts of aromatic sulfonic acids, e.g., ligninsulfonic acid,phenolsulfonic acid, naphthalenesulfonic acid anddibutylnaphthalenesulonic acid, and of fatty acids, alkyl and alkylarylsulfonates, and alkyl, lauryl ether and fatty alcohol sulfates, andsalts of sulfated hexadecanols, heptadecanols, and octadecanols, saltsof fatty alcohol glycol ethers, condensation products of sulfonatednaphthalene and naphthalene derivatives with formaldehyde, condensationproducts of naphthalene or naphthalenesulfonic acids with phenol andformaldehyde, polyoxyethylene octylphenol ethers, ethoxylatedisooctylphenol, ethoxylated octylphenol and ethoxylated nonylphenol,alkylphenol polyglycol ethers, tributylphenyl polyglycol ethers,alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcoholethylene oxide condensates, ethoxylated castor oil, polyoxyethylenealkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycolether acetal, sorbitol esters, lignin-sulfite waste liquors and methylcellulose.

Powders, dusts and broadcasting agents may be prepared by mixing orgrinding the active ingredients with a solid carrier.

Granules, e.g., coated, impregnated or homogeneous granules, may beprepared by bonding the active ingredients to solid carriers. Examplesof solid carriers are mineral earths such as silicic acids, silica gels,silicates, talc, kaolin, attapulgus clay, limestone, lime, chalk, bole,loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesiumsulfate, magnesium oxide, ground plastics, fertilizers such as ammoniumsulfate, ammonium phosphate, ammonium nitrate, and ureas, and vegetableproducts such as grain meals, bark meal, wood meal, and nutshell meal,cellulosic powders, etc.

Examples of formulations are as follows:

I. A solution of 90 parts by weight of compound no. 2 and 10 parts byweight of N-methyl-α-pyrrolidone, which is suitable for application inthe form of very fine drops.

II. A mixture of 20 parts by weight of compound no. 1/110, 80 parts byweight of xylene, 10 parts by weight of the adduct of 8 to 10 moles ofethylene oxide and 1 mole of oleic acid-N-monoethanolamide, 5 parts byweight of the calcium salt of dodecylbenzenesulfonic acid, and 5 partsby weight of the adduct of 40 moles of ethylene oxide and 1 mole ofcastor oil. By finely dispersing the mixture in water, an aqueousdispersion is obtained.

III. An aqueous dispersion of 20 parts by weight of compound no. 6/22,40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol,20 parts by weight of the adduct of 40 moles of ethylene oxide and 1mole of castor oil.

IV. An aqueous dispersion of 20 parts by weight of compound no. 6/27, 25parts by weight of cyclohexanol, 65 parts by weight of a mineral oilfraction having a boiling point between 210° and 280° C., and 10 partsby weight of the adduct of 40 moles of ethylene oxide and 1 mole ofcastor oil.

V. A hamer-milled mixture of 80 parts by weight of compound no. 6/72, 3parts by weight of the sodium salt of diisobutylnaphthalene-α-sulfonicacid, 10 parts by weight of the sodium salt of a lignin-sulfonic acidobtained from a sulfite waste liquor, and 7 parts by weight of powderedsilica gel. By finely dispersing the mixture in water, a spray liquor isobtained.

VI. An intimate mixture of 3 parts by weight of compound no. 6/77 and 97parts by weight of particulate kaolin. The dust contains 3 wt % of theactive ingredient.

VII. An intimate mixture of 30 parts by weight of compound no. 6/78, 92parts by weight of powdered silica gel and 8 parts by weight of paraffinoil sprayed onto the surface of this silica gel. This formulation of theactive ingredient exhibits good adherence.

VIII. A stable aqueous dispersion of 40 parts by weight of compound no.6/83, 10 parts of the sodium salt of a phenolsulfonicacid-urea-formaldehyde condensate, 2 parts of silica gel and 48 parts ofwater, which dispersion can be further diluted.

IX. A stable oily dispersion of 20 parts by weight of compound no. 6/85,2 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, 8parts by weight of a fatty alcohol polyglycol ether, 2 parts by weightof the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensateand 68 parts by weight of a paraffinic mineral oil.

The novel compounds are extremely effective on a broad spectrum ofphytopathogenic fungi, in particular those from the class consisting ofthe Ascomycetes and Basidiomycetes. Some of them have a systemic actionand can be used as foliar and soil fungicides.

The fungicidal compounds are of particular interest for controlling alarge number of fungi in various crops or their seeds, especially wheat,rye, barley, oats, rice, Indian corn, lawns, cotton, soybeans, coffee,sugar cane, fruit and ornamentals in horticulture and viticulture, andin vegetables such as cucumbers, beans and cucurbits.

The compounds are applied by treating the fungi, or the seed, plants ormaterials threatened by fungus attack, or the soil with a fungicidallyeffective amount of the active ingredients.

Application is effected before or after infection of the materials,plants or seed by the fungi.

The compounds I are particularly useful for controlling the followingplant diseases:

Erysiphe graminis in cereals,

Erysiphe cichoracearum and Sphaerotheca fuliginea in cucurbits,

Podosphaera leucotricha in apples,

Uncinula necator in vines,

Puccinia species in cereals,

Rhizoctonia solani in cotton,

Ustilago species in cereals and sugar cane,

Venturia inaequalis (scab) in apples,

Helminthosporium species in cereals,

Septoria nodorum in wheat,

Botrytis cinerea (gray mold) in strawberries and grapes,

Cercospora arachidicola in groundnuts,

Pseudocercosporella herpotrichoides in wheat and barley,

Pyricularia oryzae in rice,

Phytophthora infestans in potatoes and tomatoes,

Fusarium and Verticillium species in various plants,

Plasmopara viticola in grapes,

Alternaria species in fruit and vegetables.

The novel compounds may also be used for protecting materials (timber),e.g., against Paecilomyces variotii.

The fungicidal agents generally contain from 0.1 to 95, and preferablyfrom 0.5 to 90, wt % of active ingredient.

The application rates depend on the type of effect desired, and rangefrom 0.02 to 3 kg of active ingredient per hectare.

When the active ingredients are used for treating seed, rates of 0.001to 50, and preferably from 0.01 to 10, g per kg of seed are generallyrequired.

When the agents according to the invention are used as fungicides, theymay be present together with other active ingredients such asherbicides, insecticides, growth regulators, other fungicides, orfertilizers.

When the agents according to the invention are mixed with otherfungicides, the spectrum of fungicidal action is frequently increased.

The active ingredient used for comparison purposes was methyl2-(2-methylphenyl)-2-methoxyacrylate (A)-disclosed in EP 178 826.

USE EXAMPLES Use Example 1

Action on wheat mildew

Leaves of pot-grown wheat seedlings of the "Fruhgold" variety weresprayed with aqueous liquors containing (dry basis) 80% of activeingredient and 20% of emulsifier, and dusted, 24 hours after thesprayed-on layer had dried, with spores of wheat mildew (Erysiphegraminis var. tritici). The plants were then set up in the greenhouse atfrom 20° to 22° C. and a relative humidity of from 75 to 80%. The extentof mildew spread was assessed after 7 days.

The results show that active ingredients 2 from Table 1 (1/2), 1/110,6/22, 6/27, 6/72, 6/77, 6/78, 6/83, 6/85, 6/89, 6/90, 7/36, 7/41a,7/41s, 7/43, 7/60, 7/106, 7/107, 7/111, 7/112, 7/113, 7/116, 7/130 and7/133, when applied as spray liquors containing the active ingredientsin amounts of 250 ppm, have a better fungicidal action (90%) than priorart comparative compound A (50%).

Use Example 2

Action on Plasmopara viticola

Leaves of potted vines of the Muller-Thurgau variety were sprayed withaqueous suspensions containing (dry basis) 80% of active ingredient and20% of emulsifier. To assess the duration of action, the plants were setup, after the sprayed-on layer had dried, for 8 days in the greenhouse.Then the leaves were infected with a zoospore suspension of Plasmoparaviticola. The plants were first placed for 48 hours in a watervapor-saturated chamber at 24° C. and then in a greenhouse for 5 days atfrom 20° to 30° C. To accelerate and intensify the sporangiophoredischarge, the plants were then again placed in the moist chamber for 16hours. The extent of fungus attack was then assessed on the undersidesof the leaves.

The results show that active ingredients 1/2, 1/12, 1/88, 1(115, 2/57,3/55, 6/22, 6/27, 6/72, 6/77, 6/78, 6/83, 6/85, 6/89, 6/90, 6/97, 7/36,7/41a, 7/41s, 7/43, 7/60, 7/106, 7/112, 7/113, 7/116, 7/130, 7/133, 8/70and 9/50, when applied as spray liquors containing 250 ppm of activeingredient, have a better fungicidal action (90%) than prior artcomparative agent A (0%).

We claim:
 1. A compound of the formula I ##STR22## where n is 0 or 1,Wis hydrogen, halogen, unsubstituted or substituted C₁ -C₄ -alkyl orunsubstituted or substituted C₁ -C₄ -alkoxy, X is CHOCH₃, NOCH₃, CHCH₃or CHC₂ H₅, Y is oxygen, sulfur or NR⁴, --O--NR⁴ --, --NR⁴ --O-- or--NR⁴ --NR⁵ --, Z is oxygen, NR⁶, NOR⁷ or N--NR⁸ R⁹ or, where n=1,sulfur, R¹ is hydrogen or unsubstituted or substituted C₁ -C₄ -alkyl, R²is independent of R¹ and is hydrogen unsubstituted or substituted C₁ -C₄-alkyl, unsubstituted or substituted C₃ -C₆ -cycloalkyl, unsubstitutedor substituted aryl, C₁ -C₄ -perfluoroalkyl or CO--V R³ is hydrogen,unsubstituted or substituted C₁ -C₄ -alkyl, unsubstituted or substitutedC₂ -C₄ -alkenyl, unsubstituted or substituted C₃ -C₆ -cycloalkyl,unsubstituted or substituted or fused aryl, unsubstituted or substitutedaryl-C₁ -C₄ -alkyl, or unsubstituted or substituted aryl-C₂ -C₄ -alkenylor, where n=0, cyano, C₁ -C₄ -perfluoroalkyl or unsubstituted orsubstituted C₂ -C₄ -alkynyl or, where n=1, and Y is oxygen,unsubstituted or substituted trialkylsilyl, R⁴ and R⁵ are independent ofone another and are each hydrogen, unsubstituted or substituted C₁ -C₄-alkyl or unsubstituted or substituted C₃ -C₆ -cycloalkyl, R⁶ isunsubstituted or substituted C₁ -C₄ -alkyl, or unsubstituted orsubstituted or fused aryl, R⁷ and R⁸ are each hydrogen, unsubstituted orsubstituted C₁ -C₄ -alkyl, unsubstituted or substituted C₂ -C₄ -alkenyl,unsubstituted or substituted C₂ -C₄ -alkynyl, unsubstituted orsubstituted C₃ -C₆ -cycloalkyl, unsubstituted or substituted or fusedaryl, unsubstituted or substituted aryl-C₁ -C₄ -alkyl, or COR¹⁰, R⁹ hasthe same meanings as R⁴ and is independent of R⁸, R¹⁰ is unsubstitutedor substituted C₁ -C₄ -alkyl, unsubstituted or substituted C₃ -C₆-cycloalkyl, or unsubstituted or substituted aryl, V is unsubstituted orsubstituted C₁ -C₄ -alkyl, unsubstituted or substituted aryl, hydroxyl,unsubstituted or substituted C₁ -C₄ -alkoxy, unsubstituted orsubstituted allyloxy, unsubstituted or substituted benzyloxy orunsubstituted or substituted trialkylsilyloxy and is a single bond or adouble bond.
 2. A compound as claimed in claim 1, wherein X is CHOCH₃.3. A compound as claimed in claim 1, wherein X is NOCH₃.
 4. A compoundas claimed in claim 1, wherein X is CHCH₃ or CHC₂ H₅.
 5. A compound asclaimed in claim 1, wherein the bond between the carbon atomssubstituted by R¹ and R² is a single bond.
 6. A compound as claimed inclaim 1, wherein the bond between the carbon atoms substituted by R¹ andR² is a double bond.
 7. A compound of the formula I as claimed in claim1, wherein n is 0 and R³ --(Y)_(n) --C═Z is ##STR23##
 8. A compound ofthe formula I as claimed in claim 1, wherein n is 1 and R³ --(Y)_(n)--C═Z is ##STR24##
 9. A compound of the formula II ##STR25## where W ishydrogen, chlorine, methyl or methoxy,X is CHOCH₃, NOCH₃, CHCH₃, or CHC₂H₅, Z is oxygen, NR⁶, NOR⁷ or N--NR⁸ R⁹, R¹ and R² are independent ofone another and are each hydrogen or C₁ -C₄ -alkyl, R³ is hydrogen,unsubstituted or substituted C₁ -C₄ -alkyl, unsubstituted or substitutedC₂ -C₄ -alkenyl, unsubstituted or substituted C₂ -C₄ -alkynyl,unsubstituted or substituted C₃ -C₆ -cycloalkyl, unsubstituted orsubstituted or fused aryl, unsubstituted or substituted aryl-C₁ -C₄-alkyl, or unsubstituted or substituted aryl-C₂ -C₄ -alkenyl R⁴ ishydrogen, unsubstituted or substituted C₁ -C₄ -alkyl or unsubstituted orsubstituted C₃ -C₆ -cycloalkyl, R⁶ is unsubstituted or substituted C₁-C₄ -alkyl or unsubstituted or substituted or fused aryl, R⁷ and R⁸ areeach hydrogen, unsubstituted or substituted C₁ -C₄ -alkyl, unsubstitutedor substituted C₂ -C₄ -alkenyl, unsubstituted or substituted C₂ -C₄-alkynyl, unsubstituted or substituted C₃ -C₆ -cycloalkyl, unsubstitutedor substituted or fused aryl, unsubstituted or substituted aryl-C₁ -C₄-alkyl, or COR¹⁰, R⁹ has the same meanings as R⁴ and is independent ofR⁸ and R¹⁰ is unsubstituted or substituted C₁ -C₄ -alkyl, unsubstitutedor substituted C₃ -C₆ -cycloalkyl, or unsubstituted or substituted aryl.10. A compound of the formula III ##STR26## where W is hydrogen,chlorine, methyl or methoxy,X is CHOCH₃, NOCH₃, CHCH₃, or CHC₂ H₅, Y isoxygen, sulfur or NR⁴ R¹ is hydrogen or C₁ -C₄ -alkyl, R² is hydrogen,C₁ -C₄ -alkyl or CO--V , R³ is hydrogen, unsubstituted or substituted C₁-C₄ -alkyl, unsubstituted or substituted or fused aryl, unsubstituted orsubstituted aryl-C₁ -C₄ -alkyl R⁴ is hydrogen, unsubstituted orsubstituted C₁ -C₄ -alkyl or unsubstituted or substituted C₃ -C₆-cycloalkyl and V is hydroxyl, C₁ -C₄ -alkoxy, allyloxy,trialkylsilyloxy or unsubstituted or substituted benzyloxy.
 11. Acompound as claimed in claim 9, wherean X is CHOCH₃.
 12. A compound asclaimed in claim 9, wherein X is NOCH₃.
 13. A compound as claimed inclaim 9, wherean X is CHCH₃ or CHC₂ H₅.
 14. A compound as claimed inclaim 10, wherein X is CHOCH₃.
 15. A compound as claimed in claim 10,wherein X is NOCH₃.
 16. A compound as claimed in claim 10, wherein X isCHCH₃ or CHC₂ H₅.
 17. A compound of the formula IV ##STR27## where X isCHOCH₃, NOCH₃, CHCH₃, or CHC₂ H₅,Z is oxygen, NOR⁷, R³ is hydrogen,unsubstituted or substituted C₁ -C₄ -alkyl, unsubstituted or substitutedC₂ -C₄ -alkenyl, or unsubstituted or substituted or fused aryl, R⁷ ishydrogen, unsubstituted or substituted C₁ -C₄ -alkyl, unsubstituted orsubstituted C₂ -C₄ -alkenyl, unsubstituted or substituted aryl-C₁ -C₄-alkyl, or COR¹⁰ and R¹⁰ is unsubstituted or substituted C₁ -C₄ -alkyl,or unsubstituted or substituted aryl.
 18. A compound of the formula V##STR28## where X is CHOCH₃, NOCH₃, CHCH₃, or CHC₂ H₅,Y is oxygen, NR⁴,R³ is unsubstituted or substituted C₁ -C₄ -alkyl, unsubstituted orsubstituted or fused aryl, or unsubstituted or substituted aryl-C₁ -C₄-alkyl, and R⁴ is hydrogen or C₁ -C₄ -alkyl.
 19. A compound as claimedin claim 17, wherein X is CHOCH₃.
 20. A compound as claimed in claim 17,wherein X is NOCH₃.
 21. A compound as claimed in claim 17, wherein X isCHCH₃ or CHC₂ H₅.
 22. A compound as claimed in claim 18, wherein X isCHOCH₃.
 23. A compound as claimed in claim 18, wherein X is NOCH₃.
 24. Acompound as claimed in claim 18, wherein X is CHCH₃ or CHC₂ H₅.
 25. Afungicide which contains an inert carrier and a fungicidal amount of theformula I ##STR29## where n is 0 or 1,W is hydrogen, halogen,unsubstituted or substituted C₁ -C₄ -alkyl or unsubstituted orsubstituted C₁ -C₄ -alkoxy, X is CHOCH₃, NOCH₃, CHCH₃ or CHC₂ H₅, Y isoxygen, sulfur or NR⁴, --O--NR⁴ --, --NR⁴ --O-- or --NR⁴ --NR⁵ --, Z isoxygen, NR⁶, NOR⁷ or N--NR⁸ R⁹ or, where n=1, sulfur, R¹ is hydrogen orunsubstituted or substituted C₁ -C₄ -alkyl, R² is independent of R¹ andis hydrogen unsubstituted or substituted C₁ -C₄ -alkyl, unsubstituted orsubstituted C₃ -C₆ -cycloalkyl, unsubstituted or substituted aryl, or C₁-C₄ -perfluoroalkyl or CO--V R³ is hydrogen, unsubstituted orsubstituted C₁ -C₄ -alkyl, unsubstituted or substituted C₂ -C₄ -alkenyl,unsubstituted or substituted C₃ -C₆ -cycloalkyl, unsubstituted orsubstituted or fused aryl, unsubstituted or substituted aryl-C₁ -C₄-alkyl, unsubstituted or substituted aryl-C₂ -C₄ -alkenyl or, where n=0,cyano, C₁ -C₄ -perfluoroalkyl or unsubstituted or substituted C₂ -C₄-alkynyl or, where n=1, and Y is oxygen, unsubstituted or substitutedtrialkylsilyl, R⁴ and R⁵ are independent of one another and are eachhydrogen, unsubstituted or substituted C₁ -C₄ -alkyl or unsubstituted orsubstituted C₃ -C₆ -Cycloalkyl, R⁶ is unsubstituted or substituted C₁-C₄ -alkyl, unsubstituted or substituted or fused aryl, R⁷ and R⁸ areeach hydrogen, unsubstituted or substituted C₁ -C₄ -alkyl, unsubstitutedor substituted C₂ -C₄ -alkenyl, unsubstituted or substituted C₂ -C₄-alkynyl, unsubstituted or substituted C₃ -C₆ -cycloalkyl, unsubstitutedor substituted or fused aryl, unsubstituted or substituted aryl-C₁ -C₄-alkyl, or COR¹⁰, R⁹ has the same meanings as R⁴ and is independent ofR⁸, R¹⁰ is unsubstituted or substituted C₁ -C₄ -alkyl, unsubstituted orsubstituted C₃ -C₆ -cycloalkyl, or unsubstituted or substituted aryl, Vis unsubstituted or substituted C₁ -C₄ -alkyl, unsubstituted orsubstituted aryl, hydroxyl, unsubstituted or substituted C₁ -C₄ -alkoxy,unsubstituted or substituted allyloxy, unsubstituted or substitutedbenzyloxy or unsubstituted or substituted trialkylsilyloxy.
 26. A methodfor controlling fungi, wherein a fungicidal amount of a compound of theformula I ##STR30## where n is 0 or 1,W is hydrogen, halogen,unsubstituted or substituted C₁ -C₄ -alkyl or unsubstituted orsubstituted C₁ -C₄ -alkoxy, X is CHOCH₃, NOCH₃, CHCH₃ or CHC₂ H₅, Y isoxygen, sulfur or NR⁴, --O--NR⁴ --, --NR⁴ --O-- or --NR⁴ --NR⁵ --, Z isoxygen, NR⁶, NOR⁷ or N--NR⁸ R⁹ or, where n=1, sulfur, R¹ is hydrogen orunsubstituted or substituted C₁ -C₄ -alkyl, R² is independent of R¹ andis hydrogen unsubstituted or substituted C₁ -C₄ -alkyl, unsubstituted orsubstituted C₃ -C₆ -cycloalkyl, unsubstituted or substituted aryl, C₁-C₄ -perfluoroalkyl or CO--V R³ is hydrogen, unsubstituted orsubstituted C₁ -C₄ -alkyl, unsubstituted or substituted C₂ -C₄ -alkenyl,unsubstituted or substituted C₃ -C₆ -cycloalkyl, unsubstituted orsubstituted or fused aryl, unsubstituted or substituted aryl-C₁ -C₄-alkyl, unsubstituted or substituted aryl-C₂ -C₄ -alkenyl or, where n=0,cyano, C₁ -C₄ -perfluoroalkyl or unsubstituted or substituted C₂ -C₄-alkynyl or, where n=1, and Y is oxygen, unsubstituted or substitutedtrialkylsilyl, R⁴ and R⁵ are independent of one another and are eachhydrogen, unsubstituted or substituted C₁ -C₄ -alkyl or unsubstituted orsubstituted C₃ -C₆ -cycloalkyl, R⁶ is unsubstituted or substituted C₁-C₄ -alkyl, or unsubstituted or substituted or fused aryl, R⁷ and R⁸ areeach hydrogen, unsubstituted or substituted C₁ -C₄ -alkyl, unsubstitutedor substituted C₁ -C₄ -alkenyl, unsubstituted or substituted C₂ -C₄-alkynyl, unsubstituted or substituted C₃ -C₆ -cycloalkyl, unsubstitutedor substituted or fused aryl, unsubstituted or substituted aryl-C₁ -C₄-alkyl, or COR¹⁰, R⁹ has the same meanings as R⁴ and is independent ofR⁸, R¹⁰ is unsubstituted or substituted C₁ -C₄ -alkyl, unsubstituted orsubstituted C₃ -C₆ -cycloalkyl, or unsubstituted or substituted aryl, Vis unsubstituted or substituted C₁ -C₄ -alkyl, unsubstituted orsubstituted aryl, hydroxyl, unsubstituted or substituted C₁ -C₄ -alkoxy,unsubstituted or substituted allyloxy, unsubstituted or substitutedbenzyloxy or unsubstituted or substituted trialkylsilyloxy is allowed toact on the fungi or plants, seeds or materials threatened by fungalattack or on the soil.